As-Indacen Derivatives

ABSTRACT

The present invention relates to compounds of the formula I  
                 
where 
     X 1 , X 2 , R 1 , R 2 , A 1 , A 2 , Z 1 , Z 2 , m, n and rings B and B′ are as defined in claim  1.

The present invention relates to as-indacene derivatives, to liquid-crystalline media comprising these derivatives, and to electro-optical display elements containing these liquid-crystalline media. In particular, the invention relates to as-indacene derivatives of negative dielectric anisotropy.

Liquid crystals have found widespread use since the first commercially usable liquid-crystalline compounds were found about 30 years ago. Known areas of application are, in particular, displays for watches and pocket calculators, and large display panels as used in railway stations, airports and sports arenas. Further areas of application are displays of portable computers and navigation systems and video applications. For the last-mentioned applications in particular, high demands are made of the response times and contrast of the images.

The spatial arrangement of the molecules in a liquid crystal has the effect that many of its properties are direction-dependent. Of particular importance for use in liquid-crystal displays are the optical, dielectric and elasto-mechanical anisotropies. Depending on whether the molecules are oriented with their longitudinal axes perpendicular or parallel to the two plates of a capacitor, the latter has a different capacitance; in other words, the dielectric constant ε of the liquid-crystalline medium has different values for the two orientations. Substances whose dielectric constant is greater when the longitudinal axes of the molecules are oriented perpendicular to the capacitor plates than when they are oriented parallel are referred to as dielectrically positive. In other words, if the dielectric constant ε_(∥) parallel to the longitudinal axes of the molecules is greater than the dielectric constant ε_(⊥) perpendicular to the longitudinal axes of the molecules, the dielectric anisotropy Δε=ε_(∥)−ε_(⊥) is greater than zero. Most liquid crystals used in conventional displays fall into this group.

Both the polarisability of the molecule and the permanent dipole moment play a role for the dielectric anisotropy. On application of a voltage to the display, the longitudinal axis of the molecules orients itself in such a way that the larger of the dielectric constants becomes effective. The strength of the interaction with the electric field depends on the difference between the two constants. In the case of small differences, higher switching voltages are necessary than in the case of large differences. The introduction of suitable polar groups, such as, for example, nitrile groups or fluorine, into the liquid-crystal molecules enables a broad range of working voltages to be achieved.

In the case of the liquid-crystalline molecules used in conventional liquid-crystal displays, the dipole moment oriented along the longitudinal axis of the molecules is larger than the dipole moment oriented perpendicular to the longitudinal axis of the molecules. In the most widespread TN (“twisted nematic”) cells, a liquid-crystalline layer with a thickness of only from about 5 to 10 μm is arranged between two plane-parallel glass plates, onto each of which an electrically conductive, transparent layer of tin oxide or indium tin oxide (ITO) has been vapour-deposited as electrode. A likewise transparent alignment layer, usually consisting of a plastic (for example polyimides), is located between these films and the liquid-crystalline layer. This alignment layer serves to bring the longitudinal axes of the adjacent liquid-crystalline molecules into a preferential direction through surface forces in such a way that, in the voltage-free state, they lie uniformly with the same orientation, flat or with the same small tilt angle, on the inside of the display surface. Two polarisation films which only enable linear-polarised light to enter and escape are applied to the outside of the display in a certain arrangement.

By means of liquid crystals in which the larger dipole moment is oriented parallel to the longitudinal axis of the molecule, very high-performance displays have already been developed. In most cases here, mixtures of from 5 to 20 components are used in order to achieve a sufficiently broad temperature range of the mesophase and short response times and low threshold voltages. However, difficulties are still caused by the strong viewing-angle dependence in liquid-crystal displays as are used, for example, for laptops. The best imaging quality can be achieved if the surface of the display is perpendicular to the viewing direction of the observer.

If the display is tilted relative to the observation direction, the imaging quality deteriorates drastically under certain circumstances. For greater comfort, attempts are being made to maximise the angle through which the display can be tilted from the viewing direction of an observer without significantly reducing the imaging quality. Attempts have recently been made to improve the viewing-angle dependence using liquid-crystalline compounds whose dipole moment perpendicular to the longitudinal axis of the molecule is larger than that parallel to the longitudinal axis of the molecule. The dielectric anisotropy Δε is negative. In the field-free state, these molecules are oriented with their longitudinal axes perpendicular to the glass surface of the display. Application of an electric field causes them to orient themselves more or less parallel to the glass surfaces. By achieving a plurality of domains, it has been possible to achieve an improvement in the viewing-angle dependence using liquid-crystalline media of negative dielectric anisotropy. This technology can also be used to achieve shorter response times in displays and better contrast values. Displays of this type are known as VA-TFT (“vertically aligned”) displays.

Development in the area of liquid-crystalline materials is still far from complete. In order to improve the properties of liquid-crystalline display elements, attempts are constantly being made to develop novel compounds which enable optimisation of such displays.

DE 25 14 389 A discloses, inter alia, 7-substituted 6-oxo-6H-indeno[5,4-b]furancarboxylic acids and the use thereof as medicaments; neither mesogenic properties nor the use of these compounds in liquid-crystalline media are described.

J. Heterocycl. Chem., 15 (1978) 43-48, discloses 2,7-dimethylbenzo[1,2-b:4,3-b′]difuran and 4-chloro-2,7-dimethylbenzo[1,2-b:4,3-b′]difuran; neither mesogenic properties nor the use of these compounds in liquid-crystalline media are described.

EP 1 350 780 A1 describes in general 1,7-dihydroindacene derivatives of negative dielectric anisotropy, without the physical or electro-optical properties being specified in detail.

An object of the present invention is to provide compounds having advantageous properties for use in liquid-crystalline media. In particular, they should have negative dielectric anisotropy, which makes them particularly suitable for use in liquid-crystalline media for VA displays.

This object is achieved in accordance with the invention by compounds of the general formula I

in which:

independently of one another, stand for

-   A¹ and A² each, independently of one another, denote 1,4-phenylene,     in which ═CH— may be replaced once or twice by ═N— and which may be     unsubstituted or mono- to tetrasubstituted, independently of one     another, by —CN, F, Cl, Br and/or I, C₁-C₆-alkanyl which is     unsubstituted or mono- or polysubstituted by fluorine and/or     chlorine or by C₁-C₆-alkoxy which is unsubstituted or mono- or     polysubstituted by fluorine and/or chlorine, 1,4-cyclohexylene,     1,4-cyclohexenylene or 1,4-cyclohexadienylene, in which —CH₂— may be     replaced once or twice, independently of one another, by —O— or —S—     in such a way that hetero atoms are not linked directly and which     may be unsubstituted or mono- or polysubstituted by F, Cl, Br and/or     I; -   Z¹ and Z² each, independently of one another, denote a single bond,     a double bond, —CF₂O—, —OCF₂—, —CH₂CH₂—, —CF₂CF₂—, —CF₂CH₂—,     —CH₂CF₂—, —CHF—CHF—, —C(O)O—, —OC(O)—, —CH₂O—, —OCH₂—, —CF═CH—,     —CH═CF—, —CF═CF—, —CH═CH— or —C≡C—; -   R¹ and R² denote hydrogen, an alkanyl, alkoxy, alkenyl or alkynyl     radical having 1 to 15 or 2 to 15 C atoms respectively, each of     which is unsubstituted, monosubstituted by —CN or —CF₃ or     monosubstituted or polysubstituted by F, Cl, Br and/or I, where, in     addition, one or more CH₂ groups in these radicals may each be     replaced, independently of one another, by —O—, —S—, —SO₂—, —CO—,     —COO—, —OCO— or —OCO—O— in such a way that hetero atoms in the chain     are not linked directly, F, Cl, Br, I, —CN, —SCN, —NCS or —SF₅; -   m and n, independently of one another, are 0, 1, 2 or 3; -   X¹, X² and Y² each, independently of one another, denote hydrogen,     an alkanyl, alkoxy, alkenyl or alkynyl radical having 1 to 15 or 2     to 15 C atoms respectively, each of which is unsubstituted or     monosubstituted or polysubstituted by F, Cl, Br and/or I, where, in     addition, one or more CH₂ groups in these radicals may each be     replaced, independently of one another, by —O—, —S—, —SO₂—, —CO—,     —COO—, —OCO— or —OCO—O— in such a way that hetero atoms in the chain     are not linked directly, F, Cl, Br, I, —CN, —SF₅, —SCN or —NCS; -   Y¹ is as defined for Y² or stands for -[-Z³-A³-]_(p)-R³, where Z³ is     as defined for Z¹ and Z², A³ is as defined for A¹ and A², R³ is as     defined for R¹ and R², and p is as defined for n and m;     where -   A¹, A², A³, Z¹, Z², Z³, R¹, R² and R³ may each have identical or     different meanings if m, n and p respectively are greater than 1; -   Y¹ and Y² may each have identical or different meanings for rings B     and B′;     and where -   (a) R¹ does not stand for —COOH if ring B stands for ring f or g and     ring B′ stands for ring d and at the same time m is zero and X² is     not H, or R² does not stand for —COOH if ring B′ stands for ring f     or g and ring B stands for ring d and n is zero and X¹ is not H; -   (b) R¹-[-A¹-Z¹-]_(m)— and -[-Z²-A²-]-R² are not simultaneously CH₃     if one of X¹ and X² is hydrogen and the other of X¹ and X² is     hydrogen or Cl and at the same time both rings B and B′ stand for     ring g.

The compounds have negative Δε and are therefore suitable, in particular, for use in VA-TFT displays. The compounds according to the invention preferably have a Δε of <−2 and particularly preferably a Δε of <−5. They exhibit very good compatibility with the usual substances used in liquid-crystal mixtures for displays.

Furthermore, the compounds of the formula I according to the invention have values for the optical anisotropy Δn which are particularly suitable for use in VA-TFT displays. The compounds according to the invention preferably have a Δn of greater than 0.02 and less than 0.25.

The other physical, physicochemical or electro-optical parameters of the compounds according to the invention are also advantageous for use of the compounds in liquid-crystalline media. The compounds have, in particular, a sufficient breadth of the nematic phase and good low-temperature and long-term stability as well as sufficiently high clearing points and good viscosities and response times.

It is preferred for at least one of the radicals X¹ and X² on the central aromatic six-membered ring of the compound of the formula I to be other than hydrogen.

It is furthermore preferred for at least one of rings B and B′ to have at least one electronegative radical (for example —F, —Cl or ═O or halogen-substituted alkyl radicals). It is particularly preferred for both rings B and B′ to have electronegative radicals.

The radicals X¹ and X², preferably —CF₃, —OCF₃, fluorine and/or chlorine substituents, in particular fluorine substituents, on the central aromatic six-membered ring and the preferably electronegative radicals on ring B or B′ produce a dipole moment perpendicular to the longitudinal axis of the molecule, which can optionally be further strengthened by suitable substituents in the wing units -(Z¹-A¹-)_(m)-R¹ and -(Z²-A²-)_(n)-R². In the field-free state, the compounds of the formula I orient themselves with their longitudinal molecular axis perpendicular to the treated or coated glass surface of the display.

Preferred compounds of the formula I according to the invention are those in which rings B and B′ are each, independently of one another, selected from

and

where Y¹ and Y² are as defined above for the formula I. It is particularly preferred here for rings B and B′ to be identical, where the radical Y¹ in the two rings may have identical or different meanings and the radical Y² in the two rings may have identical or different meanings.

Y¹ and Y² are particularly preferably, independently of one another, F, Cl or a (per)fluorinated alkanyl or alkoxy radical having up to 6 carbon atoms, in particular —CF₃ or —OCF₃. Furthermore, Y¹ is particularly preferably also -[-Z³-A³-]_(p)-R³. Y¹ and Y² in at least one of the rings B and B′ are very particularly preferably F, in particular in both rings.

It is furthermore preferred for the compounds of the formula I according to the invention to be selected from the group consisting of compounds of the following formulae:

where

-   X¹, X², R¹, R², A¹, A², Z¹, Z², m and n are as defined in claim 1     and as defined above for the formula I; -   Y¹¹ and Y¹² are as defined for Y¹ in claim 1 and as defined above     for the formula I and can have identical or different meanings; and -   Y²¹ and Y²² are as defined for Y² in claim 1 and as defined above     for the formula I and can have identical or different meanings.

Y¹¹, Y¹², Y²¹ and Y²² are particularly preferably, independently of one another, H, F, Cl or a (per)fluorinated alkanyl or alkoxy radical having up to 6 carbon atoms, in particular —CF₃ or —OCF₃. Furthermore, Y¹¹ and Y¹² particularly preferably also stand for -[-Z³-A³-]_(p)-R³. Y¹¹ and Y²¹ or Y¹² and Y²² are very particularly preferably identical and are in particular fluorine. In particular, Y¹¹, Y²¹, Y¹² and Y²² are all simultaneously fluorine.

Particular preference is given to compounds of the formulae Iaa, Ibb, Iee, Iff and Igg.

In the compounds of the general formula I and of the formulae Iaa, Iaf, Iag, Ibb, Ibf, Ibg, Icc, Idd, Iee, Iff and Igg according to the invention, Z¹ and Z² and—if present—Z³ preferably, independently of one another, stand for a single bond, —CF₂O—, —OCF₂—, —CF₂CF₂—, —CH═CH—, —CF═CH—, —CH═CF— or —CF═CF—, particularly preferably a single bond, —CF₂O— or —OCF₂—, in particular a single bond.

In the compounds of the formula I and of the formulae Iaa, Iaf, Iag, Ibb, Ibf, Ibg, Icc, Idd, Iee, Iff and Igg according to the invention, A¹, A² and—if present—A³ are preferably, independently of one another, optionally substituted 1,4-phenylene, optionally substituted 1,4-cyclohexylene, in which —CH₂— may be replaced once or twice by —O—, or optionally substituted 1,4-cyclohexenylene. In the case where m>1, the rings A¹ may adopt identical or different meanings. In the case where n>1, the rings A² may adopt identical or different meanings. In the case where p>1, the rings A³ may adopt identical or different meanings.

A¹, A² and—if present—A³ are particularly preferably, independently of one another,

A¹, A² and—if present—A³ are very particularly preferably 1,4-cyclohexylene rings and/or optionally fluorine-substituted 1,4-phenylene rings.

R¹, R², R³, X¹, X², Y¹ and Y² in the formula I may each, independently of one another, be an alkanyl radical and/or an alkoxy radical (alkyloxy radical) having 1 to 15 C atoms which is straight-chain or branched. It is preferably straight-chain, has 1, 2, 3, 4, 5, 6 or 7 C atoms and is accordingly preferably methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy or heptoxy.

R¹, R², R³, X¹, X², Y¹ and Y² in the formula I may each, independently of one another, be oxaalkyl—i.e. one of the non-terminal CH₂ groups of the alkanyl radical has been replaced by —O——preferably straight-chain 2-oxapropyl (=methoxymethyl), 2-(=ethoxymethyl) or 3-oxabutyl (=methoxyethyl), 2-, 3- or 4-oxapentyl, 2-, 3-, 4- or 5-oxahexyl, or 2-, 3-, 4-, 5- or 6-oxaheptyl. In a corresponding manner, R¹, R², R³, X¹, X², Y¹, and Y² in the formula I may also, independently of one another, be thioalkanyl or sulfonylalkanyl radicals, i.e. alkanyl radicals in which one CH₂ group has been replaced by —S— or —SO₂—.

R¹, R², R³, X¹, X², Y¹ and Y² in the formula I may furthermore each, independently of one another, be an alkenyl radical having 2 to 15 C atoms which is straight-chain or branched and has at least one C—C double bond. It is preferably straight-chain and has 2 to 7 C atoms. Accordingly, it is preferably vinyl, prop-1- or -2-enyl, but-1-, -2- or -3-enyl, pent-1-, -2-, -3- or 4-enyl, hex-1-, -2-, -3-, -4- or -5-enyl, or hept-1-, -2-, -3-, 4-, -5- or -6-enyl. If the two C atoms of the C—C double bond are substituted, the alkenyl radical can be in the form of the E and/or Z isomer (trans/cis). In general, the respective E isomers are preferred.

R¹, R², R³, X¹, X², Y¹ and Y² in the formula I may also, independently of one another, be an alkynyl radical having 2 to 15 C atoms which is straight-chain or branched and has at least one C—C triple bond.

R¹, R², R³, X¹, X², Y¹ and Y² in the formula I may each, independently of one another, be an alkanyl radical having 1 to 15 C atoms in which one CH₂ group has been replaced by —O— and one has been replaced by —CO—, these preferably being adjacent. This thus contains an acyloxy group —CO—O— or an oxycarbonyl group —O—CO—. This radical is preferably straight-chain and has 2 to 6 C atoms. The following of these radicals are preferred here: acetoxy, propionyloxy, butyryloxy, pentanoyloxy, hexanoyloxy, acetoxymethyl, propionyloxymethyl, butyryloxymethyl, pentanoyloxymethyl, 2-acetoxyethyl, 2-propionyloxyethyl, 2-butyryloxyethyl, 2-acetoxypropyl, 3-propionyloxypropyl, 4-acetoxybutyl, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, pentoxycarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, butoxycarbonylmethyl, 2-(methoxycarbonyl)ethyl, 2-(ethoxycarbonyl)ethyl, 2-(propoxycarbonyl)ethyl, 3-(methoxycarbonyl)propyl, 3-(ethoxycarbonyl)propyl and 4-(methoxycarbonyl)butyl. Furthermore, an alkanyl radical can also have an —O—CO—O— unit. Replacement of a CH₂ group by only one —CO— group (carbonyl function) is also possible.

R¹, R², R³, X¹, X², Y¹ and Y² in the formula I may each, independently of one another, be an alkenyl radical having 2 to 15 C atoms in which a CH₂ group in the vicinity of an unsubstituted or substituted —C═C— unit has been replaced by —CO— or —CO—O— or —O—CO—, where this radical may be straight-chain or branched. The radical is preferably straight-chain and has 4 to 13 C atoms. Particular preference is given here to acryloyloxymethyl, 2-acryloyloxyethyl, 3-acryloyloxypropyl, 4-acryloyloxybutyl, 5-acryloyloxypentyl, 6-acryloyloxyhexyl, 7-acryloyloxyheptyl, 8-acryloyloxyoctyl, 9-acryloyloxynonyl, methacryloyloxymethyl, 2-methacryloyloxyethyl, 3-methacryloyloxypropyl, 4-methacryloyloxybutyl, 5-methacryloyloxypentyl, 6-methacryloyloxyhexyl, 7-methacryloyloxyheptyl and 8-methacryloyloxyoctyl. Correspondingly, a CH₂ group in the vicinity of a substituted —C—C-unit in an alkynyl radical may also be replaced by —CO—, —CO—O—, —O—CO— or —O—CO—O—.

R¹, R² and R³ in the formula I may each, independently of one another, be an alkanyl radical having 1 to 15 C atoms or alkenyl radical having 2 to 15 C atoms which is monosubstituted by —CN or —CF₃, where these are preferably straight-chain. The substitution by —CN or —CF₃ is possible in any desired position.

R¹, R², R³, X¹, X², Y¹ and Y² in the formula I may each, independently of one another, be an alkanyl radical in which two or more CH₂ groups have been replaced by —O— and/or —CO—O—, where this may be straight-chain or branched. It is preferably branched and has 3 to 12 C atoms.

R¹, R², R³, X¹, X², Y¹ and Y² in the formula I may each, independently of one another, be an alkanyl radical having 1 to 15 C atoms or an alkenyl radical having 2 to 15 C atoms which is monosubstituted or polysubstituted by F, Cl, Br and/or I, where these radicals are preferably straight-chain and halogen is preferably —F and/or —Cl. In the case of polysubstitution, halogen is preferably —F. The resultant radicals also include perfluorinated radicals, such as —CF₃. In the case of monosubstitution, the fluorine or chlorine substituent can be in any desired position, but is preferably in the ω position.

R¹, R², R³, X¹, X², Y¹ and Y² in the formula I may also each, independently of one another, be —F, —Cl, —Br, —I, —CN, —SCN, —NCS or —SF₅.

R¹, R² and R³ in the general formula I are particularly preferably, independently of one another, an alkanyl radical, alkoxy radical or alkenyl radical having 1 to 7 or 2 to 7 C atoms respectively.

X¹ and X² in the general formula I are preferably, independently of one another, hydrogen, an alkanyl radical, alkoxy radical or alkenyl radical having 1 to 7 or 2 to 7 C atoms respectively, each of which is at least monosubstituted by halogen, or a halogen. It is particularly preferred here for at least one of X¹ and X² to be —CF₃, —OCF₃, F or Cl. Very particularly preferably, both radicals X¹ and X² are —CF₃, —OCF₃, fluorine or chlorine, and in particular both are fluorine.

Preferred compounds of the general formula I have a total of zero, one, two or three wing units -Z¹-A¹- and -Z²-A²-, i.e. n+m=0, 1, 2 or 3, where n and m are each 0, 1, 2 or 3. If two or three wing units are present, they may be bonded to only one side of the molecule, i.e. to ring B or to ring B′, or alternatively to both sides of the molecule. Particularly preferably, n+m=0 or 1.

In connection with the present invention, halogen denotes fluorine, chlorine, bromine and iodine.

In connection with the present invention, the term “alkyl”—unless defined otherwise elsewhere in this description or in the claims—denotes a straight-chain or branched aliphatic hydrocarbon radical having 1 to 15 (i.e. 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15) carbon atoms; this radical is unsubstituted or monosubstituted or polysubstituted by fluorine, chlorine, bromine, iodine, carboxyl, nitro, —NH₂, —N(alkanyl)₂ and/or cyano, where the polysubstitution can take place with identical or different substituents. If this alkyl radical is a saturated radical, it is also referred to as “alkanyl”. Furthermore, the term “alkyl” also encompasses hydrocarbon radicals which are unsubstituted or correspondingly mono- or polysubstituted by identical or different substituents, in particular by F, Cl, Br, I and/or —CN, and in which one or more CH₂ groups may be replaced by —O— (“alkoxy”, “oxaalkyl”), —S— (“thioalkyl”), —SO₂—, —CH═CH— (“alkenyl”), —C═C— (“alkynyl”), —CO—, —CO—O—, —O—CO— or —O—CO—O— in such a way that hetero atoms (O or S) in the chain are not linked directly to one another. Alkyl is preferably a straight-chain or branched, unsubstituted or substituted alkanyl, alkenyl or alkoxy radical having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms.

Since one or more CH₂ groups in an alkyl radical may be replaced by —O—, the term “alkyl” also encompasses “alkoxy” or “oxaalkyl” radicals. In connection with the present invention—if the term is not defined otherwise elsewhere in the description or in the claims—the term alkoxy is taken to mean an O-alkyl radical in which the oxygen atom is bonded directly to the alkoxy-substituted group or the substituted ring and alkyl is as defined above; alkyl is preferably then alkanyl or alkenyl. Preferred alkoxy radicals are methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy and octoxy, where each of these radicals may also be substituted, preferably by one or more fluorine atoms. Alkoxy is particularly preferably —OCH₃, —OC₂H₅, —O-n-C₃H₇, —O-n-C₄H₉, —O-t-C₄H₉, —OCF₃, —OCHF₂, —OCHF or —OCHFCHF₂. In connection with the present invention, the term “oxaalkyl”—if the term is not defined otherwise elsewhere in the description or in the claims—denotes alkyl radicals in which at least one non-terminal CH₂ group has been replaced by —O— in such a way that there are no adjacent hetero atoms (O or S). Oxaalkyl preferably encompasses straight-chain radicals having 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 carbon atoms.

In connection with the present invention, the term “alkenyl”—unless defined otherwise in the claims or elsewhere in this description—denotes an alkyl radical as defined above in which one or more —CH═CH— groups are present. If two —CH═CH— groups are present in the radical, this may also be referred to as “alkadienyl”. An alkenyl radical can contain 2 to 15 (i.e. 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15) carbon atoms and is branched or preferably straight-chain. The radical is unsubstituted or mono- or polysubstituted by identical or different substituents, in particular by F, Cl, Br, I and/or CN. Furthermore, one or more CH₂ groups may each, independently of one another, be replaced by —O—, —S—, —C═C—, —CO—, —CO—O—, —O—CO—, —O—CO—O— in such a way that hetero atoms (O or S) are not bonded directly to one another. If the CH═CH group carries a radical other than hydrogen on both carbon atoms, for example if it is a non-terminal group, the CH═CH group can exist in two configurations, namely as the E isomer and as the Z isomer. In general, the E isomer (trans) is preferred. The alkenyl radical preferably contains 2, 3, 4, 5, 6 or 7 carbon atoms and denotes vinyl, 1E-propenyl, 1E-butenyl, 1E-pentenyl, 1E-hexenyl, 1E-heptenyl, 2-propenyl, 2E-butenyl, 2E-pentenyl, 2E-hexenyl, 2E-heptenyl, 3-butenyl, 3E-pentenyl, 3E-hexenyl, 3E-heptenyl, 4-pentenyl, 4Z-hexenyl, 4E-hexenyl, 4Z-heptenyl, 5-hexenyl or 6-heptenyl.

If one or more CH₂ groups in an alkyl radical have been replaced by —C≡C—, an alkynyl radical is present. Replacement of one or more CH₂ groups by —CO—O— or —O—CO— is also possible. The following of these radicals are preferred here: acetoxy, propionyloxy, butyryloxy, pentanoyloxy, hexanoyloxy, acetoxymethyl, propionyloxymethyl, butyryloxymethyl, pentanoyloxymethyl, 2-acetoxyethyl, 2-propionyloxyethyl, 2-butyryloxyethyl, 2-acetoxypropyl, 3-propionyloxypropyl, 4-acetoxybutyl, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, pentoxycarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, butoxycarbonylmethyl, 2-(methoxycarbonyl)ethyl, 2-(ethoxycarbonyl)ethyl, 2-(propoxycarbonyl)ethyl, 3-(methoxycarbonyl)propyl, 3-(ethoxycarbonyl)propyl and 4-(methoxycarbonyl)butyl.

If one CH₂ group in an alkyl radical has been replaced by unsubstituted or substituted —CH═CH— and an adjacent CH₂ group has been replaced by CO, CO—O or O—CO, this radical may be straight-chain or branched. It is preferably straight-chain and has 4 to 12 C atoms. Accordingly, it particularly preferably denotes acryloyloxymethyl, 2-acryloyloxyethyl, 3-acryloyloxypropyl, 4-acryloyloxybutyl, 5-acryloyloxypentyl, 6-acryloyloxyhexyl, 7-acryloyloxyheptyl, 8-acryloyloxyoctyl, 9-acryloyloxynonyl, methacryloyloxymethyl, 2-methacryloyloxyethyl, 3-methacryloyloxypropyl, 4-methacryloyloxybutyl, 5-methacryloyloxypentyl, 6-methacryloyloxyhexyl, 7-methacryloyloxyheptyl or 8-methacryloyloxyoctyl.

If radicals or substituents of the compounds according to the invention or the compounds according to the invention themselves can exist as optically active or stereoisomeric radicals, substituents or compounds respectively since they have, for example, a centre of asymmetry, these are also encompassed by the present invention. It goes without saying here that the compounds of the general formula I according to the invention can exist in isomerically pure form, for example as pure enantiomers, diastereomers, E or Z isomers, trans or cis isomers, or as a mixture of a plurality of isomers in any desired ratio, for example as a racemate, E/Z isomer mixture or cis/trans isomer mixture.

The compounds of the general formula I are prepared by methods known per se, as described in the literature (for example in the standard works, such as Houben-Weyl, Methoden der organischen Chemie [Methods of Organic Chemistry], Georg-Thieme-Verlag, Stuttgart), to be precise under reaction conditions which are known and suitable for the said reactions. Use can be made here of variants which are known per se, but are not mentioned here in greater detail.

If desired, the starting materials can also be formed in situ by not isolating them from the reaction mixture, but instead immediately converting them further into the compounds of the general formula I.

The syntheses of various polysubstituted phenyl derivatives which are used to build up the as-indacene derivatives according to the invention containing the fused five-membered rings B and B′ are described by way of example in the examples. The starting substances are obtainable by generally accessible literature procedures or are commercially available. The reactions described should likewise be regarded as known from the literature.

An illustrative synthesis for building up the as-indacene skeleton is shown below. The synthesis can be adapted to the particular desired compounds of the general formula I through the choice of suitable starting materials.

Starting from the 1,2-dibromophenol derivative A, reaction with the α,β-unsaturated aldehyde B¹ in the presence of lithium diisopropylamide (LDA) gives compound C. Repetition of this reaction with the aldehyde B gives D. D reacts with palladium catalysis in the presence of triethylamine with ring closure to give the diketone E (=compound Icc). The diketone E and 1,2-ethanedithiol in the presence of BF₃/diethyl ether give the corresponding bisdithiane F. This is reacted with 1,3-dibromo-5,5-dimethylhydantoin (DBH) and HF in pyridine to give G. Elimination of HBr in the presence of diazabicycloundecene (DBU) gives the as-indacene derivative H (=compound Ibb where Y¹¹=Y¹²=Y²¹=Y²²=F). The as-indacene derivative H is hydrogenated on palladium/carbon catalyst in a hydrogen atmosphere to give the as-indacene derivative J (=compound Iaa where Y¹¹=Y¹²=Y²¹=Y²²=F).

On the one hand, reduction of the diketone E, for example using LiAlH₄, gives the alcohol K, from which on the one hand subsequent elimination using acid gives the as-indacene derivative L (=compound lee where Y¹¹=Y²¹=H) and on the other hand using DAST (diaminosulfur trifluoride; cf. M. Hudlicky, Organic Reactions, 35, 1988, 513) gives the as-indacene derivative M (=compound Iaa where Y¹¹=Y¹²=F and Y²¹=Y²²=H) analogously to the process described in DE 44 34 975 A1.

Furthermore, reaction of the diketone E with DAST analogously to the process disclosed in DE 44 34 975 A1 gives the as-indacene derivative N (=compound lee where Y¹=Y²=F).

The introduction of chlorine atoms (instead of fluorine atoms) is also possible starting from the diketone E with phosphoryl chloride with warming in dimethylformamide. Trifluoromethyl radicals are introduced analogously to the process disclosed in DE 10135499 A1 starting from the diketone E.

A further illustrative synthesis of compounds of the formula I according to the invention is shown by the following scheme:

Starting from O, a trimethylsilyl group can be introduced into the phenyl ring using n-butyllithium and trimethylsilyl chloride; subsequent reaction with the acid chloride shown with Lewis acid catalysis gives P. Depending on the meaning of the radical -[-Z³-A³-]_(p)-R³, it is introduced with formation of Q by a Wittig reaction and subsequent catalytic hydrogenation (p=0, R³=alkyl) or by reaction with a suitable organometallic compound containing -[-Z³-A³-]_(p)-R³ as structural unit, subsequent elimination of the OH group formed and final catalytic reduction. Cyclisation to give R is carried out after saponification of the ester function and conversion into an acid chloride with Lewis acid catalysis. The resultant keto function of R can be reduced by means of a Wolff-Kishner reduction, followed by silylation using trimethylsilyl chloride and reaction with the acid chloride shown to give S. Cyclisation to give T is carried out with acid catalysis. Starting from T, further compounds of the formula I according to the invention are then accessible in the manner described above.

Compounds according to the invention containing one or two oxygen-containing five-membered rings can be prepared in accordance with the following scheme or with adaptation thereof and of the syntheses described for the formation of the carbocyclic five-membered rings:

After diazotisation and introduction of the second OH group using iodine/potassium carbonate, the aromatic compound U is converted into the diiodinated aromatic compound V. With catalysis using bistriphenylphosphinepalladium(II) chloride and copper(I) iodide, the alkyne R¹-[-A¹-Z¹-]_(m)-≡ or R²-[-A²-Z²-]_(n)-≡ gives the benzodifuran W, from which X is also accessible by means of catalytic hydrogenation.

The following synthesis sequence illustrates the preparation of compounds according to the invention having an oxygen-containing five-membered ring, where recourse can be made to the preparation methods explained for the above schemes for the individual synthesis steps.

The reactions described should only be regarded as illustrative. The person skilled in the art can carry out corresponding variations of the syntheses described and also follow other suitable synthetic routes in order to obtain compounds of the formula I.

As already mentioned, the compounds of the general formula I can be used in liquid-crystalline media.

The present invention therefore also relates to a liquid-crystalline medium comprising at least two liquid-crystalline compounds, comprising at least one compound of the general formula I.

The present invention also relates to liquid-crystalline media comprising 2 to 40, preferably 4 to 30, components as further constituents besides one or more compounds of the formula I according to the invention. These media particularly preferably comprise 7 to 25 components besides one or more compounds according to the invention. These further constituents are preferably selected from nematic or nematogenic (monotropic or isotropic) substances, in particular substances from the classes of the azoxybenzenes, benzylideneanilines, biphenyls, terphenyls, 1,3-dioxanes, 2,5-tetrahydropyrans, phenyl or cyclohexyl benzoates, phenyl or cyclohexyl esters of cyclohexanecarboxylic acid, phenyl or cyclohexyl esters of cyclohexylbenzoic acid, phenyl or cyclohexyl esters of cyclohexylcyclohexanecarboxylic acid, cyclohexylphenyl esters of benzoic acid, of cyclohexanecarboxylic acid or of cyclohexylcyclohexanecarboxylic acid, phenylcyclohexanes, cyclohexylbiphenyls, phenylcyclohexylcyclohexanes, cyclohexylcyclohexanes, cyclohexylcyclohexylcyclohexenes, 1,4-biscyclohexylbenzenes, 4′,4′-biscyclohexylbiphenyls, phenyl- or cyclohexylpyrimidines, phenyl- or cyclohexylpyridines, phenyl- or cyclohexyldioxanes, phenyl- or cyclohexyl-1,3-dithianes, 1,2-diphenylethanes, 1,2-dicyclohexylethanes, 1-phenyl-2-cyclohexylethanes, 1-cyclohexyl-2-(4-phenylcyclohexyl)ethanes, 1-cyclohexyl-2-biphenylethanes, 1-phenyl-2-cyclohexylphenylethanes, optionally halogenated stilbenes, benzyl phenyl ethers, tolans and substituted cinnamic acids. The 1,4-phenylene groups in these compounds may also be mono- or polyfluorinated.

The most important compounds suitable as further constituents of media according to the invention can be characterised by the formulae (II), (III), (IV), (V) and (VI): R′-L-E-R″  (II) R′-L-COO-E-R″  (III) R′-L-OOC-E-R″  (IV) R′-L-CH₂CH₂-E-R″  (V) R′-L-CF₂O-E-R″  (VI)

In the formulae (II), (III), (IV), (V) and (VI), L and E, which may be identical or different, each, independently of one another, denote a divalent radical from the group formed by -Phe-, -Cyc-, -Phe-Phe-, -Phe-Cyc-, -Cyc-Cyc-, -Pyr-, -Dio-, -Thp-, -G-Phe- and -G-Cyc- and their mirror images, where Phe denotes unsubstituted or fluorine-substituted 1,4-phenylene, Cyc denotes trans-1,4-cyclohexylene or 1,4-cyclohexylene, Pyr denotes pyrimidine-2,5-diyl or pyridine-2,5-diyl, Dio denotes 1,3-dioxane-2,5-diyl,

Thp denotes tetrahydropyran-2,5-diyl and G denotes 2-(trans-1,4-cyclohexyl)ethyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, 1,3-dioxane-2,5-diyl or tetrahydropyran-2,5-diyl.

One of the radicals L and E is preferably Cyc or Phe. E is preferably Cyc, Phe or Phe-Cyc. The media according to the invention preferably comprise one or more components selected from the compounds of the formulae (II), (III), (IV), (V) and (VI) in which L and E are selected from the group consisting of Cyc and Phe and simultaneously one or more components selected from the compounds of the formulae (II), (III), (IV), (V) and (VI) in which one of the radicals L and E is selected from the group consisting of Cyc and Phe and the other radical is selected from the group consisting of -Phe-Phe-, -Phe-Cyc-, -Cyc-Cyc-, -G-Phe- and -G-Cyc-, and optionally one or more components selected from the compounds of the formulae (II), (III), (IV), (V) and (VI) in which the radicals L and E are selected from the group consisting of -Phe-Cyc-, -Cyc-Cyc-, -G-Phe- and -G-Cyc-.

In a smaller sub-group of the compounds of the formulae (II), (III), (IV), (V) and (VI), R′ and R″ each, independently of one another, denote alkyl, alkenyl, alkoxy, alkoxyalkyl (oxaalkyl), alkenyloxy or alkanoyloxy having up to 8 C atoms. This smaller sub-group is called group A below, and the compounds are referred to by the sub-formulae (IIa), (IIIa), (IVa), (Va) and (VIa). In most of these compounds, R′ and R″ are different from one another, one of these radicals usually being alkyl, alkenyl, alkoxy or alkoxyalkyl (oxaalkyl).

In another smaller sub-group of the compounds of the formulae (II), (III), (IV), (V) and (VI), which is known as group B, E denotes

In the compounds of group B, which are referred to by the sub-formulae (IIb), (IIIb), (IVb), (Vb) and (VIb), R′ and R″ have the meaning indicated for the compounds of the sub-formulae (IIa) to (VIa) and are preferably alkyl, alkenyl, alkoxy or alkoxyalkyl (oxaalkyl).

In a further smaller sub-group of the compounds of the formulae (II), (III), (IV), (V) and (VI), R″ denotes —CN. This sub-group is referred to below as group C, and the compounds of this sub-group are correspondingly described by the sub-formulae (IIc), (IIIc), (IVc), (Vc) and (VIc). In the compounds of the sub-formulae (IIc), (IIIc), (IVc), (Vc) and (VIc), R′ has the meaning indicated for the compounds of the sub-formulae (IIa) to (VIa) and is preferably alkyl, alkenyl, alkoxy or alkoxyalkyl (oxaalkyl).

Besides the preferred compounds of groups A, B and C, other compounds of the formulae (II), (III), (IV), (V) and (VI) having other variants of the proposed substituents are also customary. All these substances are obtainable by methods which are known from the literature or analogously thereto.

Besides the compounds of the general formula I according to the invention, the media according to the invention preferably comprise one or more compounds from groups A, B and/or C. The proportions by weight of the compounds from these groups in the media according to the invention are:

group A: 0 to 90%, preferably 20 to 90%, in particular 30 to 90%

group B: 0 to 80%, preferably 10 to 80%, in particular 10 to 70%

group C: 0 to 80%, preferably 5 to 80%, in particular 5 to 50%.

The media according to the invention preferably comprise 1 to 40%, particularly preferably 5 to 30%, of the compounds of the formula I according to the invention. Preference is furthermore given to media comprising more than 40%, in particular 45 to 90%, of compounds of the formula I according to the invention. The media preferably comprise one, two, three, four or five compounds of the formula I according to the invention.

Examples of the compounds of the formulae (II), (III), (IV), (V) and (VI) are the compounds listed below:

where R^(a) and R^(b), independently of one another, are —C_(n)H_(2n+1) or —OC_(n)H_(2n+1), and n=1, 2, 3, 4, 5, 6, 7 or 8, and L¹ and L², independently of one another, are —H or —F,

where m and n, independently of one another, are 1, 2, 3, 4, 5, 6, 7 or 8.

The media according to the invention are prepared in a manner conventional per se. In general, the components are dissolved in one another, advantageously at elevated temperature. By means of suitable additives, the liquid-crystalline phases of the present invention can be modified in such a way that they can be used in all types of liquid-crystal display element that have been disclosed hitherto. Additives of this type are known to the person skilled in the art and are described in detail in the literature (H. Kelker/R. Hatz, Handbook of Liquid Crystals, Verlag Chemie, Weinheim, 1980). For example, pleochroic dyes can be used for the production of coloured guest-host systems or substances can be added in order to modify the dielectric anisotropy, the viscosity and/or the alignment of the nematic phases.

Owing to their negative Δε, the compounds of the formula I are particularly suitable for use in VA-TFT displays.

The present invention therefore also relates to electro-optical liquid-crystal display elements containing a liquid-crystalline medium according to the invention.

The invention is explained in greater detail below with reference to working examples, but without being restricted thereby.

EXAMPLES

The starting substances can be obtained by generally accessible literature procedures or are commercially available. The reactions described are known from the literature.

Physical, physicochemical or electro-optical parameters are determined by generally known methods, as described, inter alia, in the brochure “Merck Liquid Crystals—Licristal®—Physical Properties of Liquid Crystals—Description of the Measurement Methods”, 1998, Merck KGaA, Darmstadt.

Example A

At −75° C., a solution of 13.5 g (50.0 mmol) of 1,2-dibromo-4,5-difluorobenzene 2 in 10 ml of THF is added to 27.0 ml of a solution, diluted with 100 ml, of 2N lithium diisopropylamide (LDA) in cyclohexane/ethylbenzene/THF (54.0 mmol). After 2 hours at the low temperature, 4.6 g (47.0 mmol) of the aldehyde 1 in 10 ml of THF are added. After 30 minutes, the cooling is removed, and 100 ml of 1N HCl are added to the batch at 20° C. Extraction of the aqueous phase, drying of the organic phase, evaporation and chromatography gives the allyl alcohol 3. Repetition of this reaction starting from 3 gives the bisallyl alcohol 4.

35.0 g (74.8 mmol) of the bisallyl alcohol 4, 5.5 g of bis(tri-o-tolylphosphine)palladium dichloride and 50 ml of triethylamine are dissolved in 390 ml of acetonitrile and warmed at 90° C. until the allyl alcohol has reacted completely. The cooled batch is introduced into water. Extraction, drying, evaporation and chromatography gives the diketone 5.

Example B

10.0 g (32.6 mmol) of the diketone 5 and 7.0 ml (69.9 mmol) of propane-dithiol are dissolved in 50 ml of dichloromethane, and 7.0 ml of boron trifluoride/diethyl ether complex are added at 6 to 7° C., and the mixture is subsequently stirred overnight at room temperature. The batch is added to 10 ml of saturated sodium hydrogencarbonate solution, and the mixture is stirred until the evolution of gas is complete. After extraction of the aqueous phase, drying of the organic phase, evaporation and filtration through silica gel, the residue obtained is employed in the next step without further purification.

10.0 g of the crude thioketal 6, dissolved in 30 ml of dichloromethane, are slowly added at −75° C. to a mixture of 45.8 g (160 mmol) of 1,3-dibromo-5,5-dimethylhydantoin (DBH), 80 ml of a 65% solution of hydrogen fluoride in pyridine and 50 ml of dichloromethane. The batch is subsequently stirred overnight at room temperature. The reaction mixture is added to ice-cooled hydrogen sulfite solution and deacidified using saturated sodium hydrogencarbonate solution and sodium hydroxide solution. Extraction, drying, evaporation, re-washing with water, chromatography and crystallisation from hexane gives the as-indacene derivative 7.

6.0 g (11.8 mmol) of the as-indacene derivative 7 are dissolved in 50 ml of dichloromethane, 4.5 ml (30.0 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) are added, and the mixture is stirred at room temperature until the starting material has reacted completely. The batch is washed with water and saturated sodium chloride solution, evaporated and chromatographed, and the as-indacene derivative 8 is isolated.

Example C

4.0 g (11.6 mmol) of the as-indacene derivative 8 are dissolved in 50 ml of THF and hydrogenated at room temperature and atmospheric pressure on a palladium catalyst. Evaporation, chromatography on silica gel and crystallisation gives the as-indacene derivative 9.

Example D

Under nitrogen, 116.5 g (1.00 mol) of 1,2-difluorobenzene (10) are dissolved in 600 ml of tetrahydrofuran, and 656 ml of a 15% solution of butyllithium in n-hexane (1.05 mol) are added at −70° C. After 1 h at this temperature, a solution of 132.6 ml (1.05 mol) of trimethylsilyl chloride (11) in 100 ml of tetrahydrofuran is slowly added to the reaction mixture. The batch thaws overnight and is added to 1.5 l of sat. ammonium chloride solution. The organic phase is dried over sodium sulfate and evaporated: the residue obtained is distilled at 8 mbar, giving 152 g (81%, b.p. 88° C.) of the silyl compound 12.

Under nitrogen, 37.6 g (250 mmol) of the acid chloride 13 are dissolved in 200 ml of cyclohexane. 46.6 g (250 mmol) of the silyl compound 12 are added to the solution at 0-2° C. 37.3 g (280 mmol) of aluminium chloride are subsequently added in portions to the reaction mixture, during which the temperature is held between −2° C. and 2° C. After 1 h at low temperature, the cooling is removed. The batch warms to room temperature and is transferred onto ice. The aqueous phase is extracted with methyl tert-butyl ether, and the organic phase is dried over sodium sulfate and evaporated. The residue is purified on silica gel, giving 31.4 g (55%) of the keto ester 14.

Under nitrogen, 51.1 g (150 mmol) of the Wittig salt 15 are suspended in 200 ml of THF, and a solution of 15.7 g (140 mmol) of potassium tertbutoxide in 75 ml of THF is added at 5-10° C. After one hour, the keto ester 14 dissolved in 75 ml of THF is added. The cooling is subsequently removed. After 20 h at room temp., water is added to the batch. The aqueous phase is extracted with MTB ether. The organic phase is washed with sat. sodium chloride solution, dried over sodium sulfate and evaporated. The residue is passed through silica gel (MTB ether/n-hexane 1:10), giving 29.4 g (88%) of the ester 16.

29.0 g (21.6 mmol) of the ester 16 are dissolved in 500 ml of tetrahydrofuran and hydrogenated on a palladium catalyst. The hydrogenation solution is evaporated, and the residue is chromatographed on silica gel, giving 27.8 g (95%) of substance 17.

27.0 g (105 mmol) of the ester 17 are refluxed for 5 h in ethanolic potassium hydroxide solution. The alcohol is subsequently distilled off, and the residue is taken up in water, acidified using hydrochloric acid and extracted with MTB ether. The organic phase is dried over sodium sulfate and evaporated. 50 ml of thionyl chloride and one drop of DMF are added to the residue obtained, and the mixture is refluxed until the evolution of gas is complete. Excess thionyl chloride is distilled off. The residue (25 g) is employed in the next step without further purification.

A solution of 25 g (about 105 mmol) of the crude acid chloride 18 in 120 ml of dichloromethane is added under nitrogen and at −20 to −15° C. to a suspension of 16.4 g (119 mmol) of aluminium chloride in 80 ml of dichloromethane. After 4.5 h, the reaction is terminated by addition of ice, and the mixture is acidified using hydrochloric acid. The aqueous phase is extracted with methylene chloride. The organic phase is dried over sodium sulfate and evaporated. The residue is chromatographed on silica gel (MTB/n-heptane 1:5), giving 18.5 g (84%) of the indanone 19.

23.9 g (361 mmol) of potassium hydroxide are dissolved in 90 ml of diethylene glycol. 13.0 ml (268 mmol) of hydrazinium hydroxide and 18.0 g (85.6 mmol) of the indanone 19 are added to the solution, and the mixture is refluxed for 2 h. The temperature of the heating bath is subsequently raised to 200° C. and maintained until the evolution of gas is complete. The cooled reaction mixture is poured into water and acidified. The aqueous phase is extracted with n-pentane. The organic phase is dried over sodium sulfate and evaporated. The residue is purified by chromatography on silica gel (n-pentane), giving 11.4 g (68%) of the indane 20.

The silylation of the indane 20 is carried out in accordance with the above procedure. The purification is carried out by chromatography on silica gel (n-pentane). 11.0 g (56.5 mmol) of the indane 20 give 12.6 g (84%) of the silyl compound 21.

The acylation of the silyl compound 21 is carried out in accordance with the above procedure. 12.0 g (44.7 mmol) of 21 give 6.8 g (52%) of the ketone 23.

6.5 g (22.2 mmol) of the ketone 23 are introduced into 30 l of trifluoromethanesulfonic acid with ice cooling and stirring. After 24 h, the batch is transferred onto ice and extracted with MTB ether. The organic phase is washed with sat. sodium hydrogencarbonate solution, dried over sodium sulfate and evaporated. The residue is purified on silica gel (MTB ether/n-heptane 1:8), giving 2.6 g (40%) of the indacene 24.

The further derivatisation of 24 is carried out analogously to Examples B and C.

Example E

25.0 g (172 mmol) of the aromatic compound 1 are dissolved in 10 ml of semi-conc. hydrochloric acid, and 11.9 g (172 mmol) of sodium nitrite in 70 ml of water are added at a temperature of below 5° C. When the addition of nitrite is complete, the batch is diluted with 100 ml of water and heated to the boil. When the evolution of nitrogen has subsided (bubble counter), the batch is refluxed for a further hour. The cooled reaction solution is extracted with MTB ether. The organic phase is dried over sodium sulfate and evaporated, giving 13.7 g (54%) of the diol 26.

13.0 g (90.0 mmol) of the phenol 26 and 48 g (348 mmol) of potassium carbonate are dissolved in 160 ml of water, and 50 g (200 mmol) of iodine are added in portions at 5° C. The batch is stirred overnight. The reaction solution is decanted off from the resultant precipitate and acidified using hydrochloric acid. The aqueous phase is extracted with MTB ether, washed with sat. sodium chloride solution, dried over sodium sulfate and evaporated. The residue is passed through silica gel (MTB ether/heptane 2:1), giving 20.1 g (57%) of the diiodinated aromatic compound 27.

Under nitrogen, 20.0 g (50.3 mmol) of the phenol 27 are dissolved in 120 ml of dimethylformamide and 28 ml of triethylamine, and 1.0 g of bistriphenylphosphinepalladium(II) chloride and 580 mg of copper(I) iodide are added. A solution of 10.3 ml (105 mmol) of 1-pentyne in 30 ml of dimethylformamide is subsequently added slowly to the batch. The batch is stirred at room temp. until the conversion is complete (TLC). Water is added to the reaction mixture, which is extracted with MTB ether. The organic phase is dried over sodium sulfate and evaporated. Chromatography on silica gel gives 6.5 g (46%) of the benzodifuran 28.

6.0 g (21.6 mmol) of the benzodifuran 28 are dissolved in 100 ml of tetrahydrofuran and hydrogenated on a palladium catalyst. The hydrogenation solution is evaporated, and the residue is chromatographed on silica gel, giving 5.5 g (90%) of substance 29.

The following compounds were prepared in accordance with or analogously to Examples A to E. “bond” here stands for a single bond:

Examples 1-259

Examples 260-518

Examples 519-777

Example No. X¹ X² R¹ R²  1, 260, 519, H H H CH₃  2, 261, 520, H H H C₂H₅  3, 262, 521, H H H n-C₃H₇  4, 263, 522, H H H n-C₄H₉  5, 264, 523, H H H n-C₅H₁₁  6, 265, 524, H H H n-C₆H₁₃  7, 266, 525, H H H n-C₇H₁₅  8, 267, 526, F H H CH₃  9, 268, 527, F H H C₂H₅  10, 269, 528, F H H n-C₃H₇  11, 270, 529, F H H n-C₄H₉  12, 271, 530, F H H n-C₅H₁₁  13, 272, 531, F H H n-C₆H₁₃  14, 273, 532, F H H n-C₇H₁₅  15, 274, 533, H F H CH₃  16, 275, 534, H F H C₂H₅  17, 276, 535, H F H n-C₃H₇  18, 277, 536, H F H n-C₄H₉  19, 278, 537, H F H n-C₅H₁₁  20, 279, 538, H F H n-C₆H₁₃  21, 280, 539, H F H n-C₇H₁₅  22, 281, 540, F F H CH₃  23, 282, 541, F F H C₂H₅  24, 283, 542, F F H n-C₃H₇  25, 284, 543, F F H n-C₄H₉  26, 285, 544, F F H n-C₅H₁₁  27, 286, 545, F F H n-C₆H₁₃  28, 287, 546, F F H n-C₇H₁₅  29, 288, 547, CF₃ H H CH₃  30, 289, 548, CF₃ H H C₂H₅  31, 290, 549, CF₃ H H n-C₃H₇  32, 291, 550, CF₃ H H n-C₄H₉  33, 292, 551, CF₃ H H n-C₅H₁₁  34, 293, 552, CF₃ H H n-C₆H₁₃  35, 294, 553, CF₃ H H n-C₇H₁₅  36, 295, 554, H CF₃ H CH₃  37, 296, 555, H CF₃ H C₂H₅  38, 297, 556, H CF₃ H n-C₃H₇  39, 298, 557, H CF₃ H n-C₄H₉  40, 299, 558, H CF₃ H n-C₅H₁₁  41, 300, 559, H CF₃ H n-C₆H₁₃  42, 301, 560, H CF₃ H n-C₇H₁₅  43, 302, 561, —OCF₃ H H CH₃  44, 303, 562, —OCF₃ H H C₂H₅  45, 304, 563, —OCF₃ H H n-C₃H₇  46, 305, 564, —OCF₃ H H n-C₄H₉  47, 306, 565, —OCF₃ H H n-C₅H₁₁  48, 307, 566, —OCF₃ H H n-C₆H₁₃  49, 308, 567, —OCF₃ H H n-C₇H₁₅  50, 309, 568, H —OCF₃ H CH₃  51, 310, 569, H —OCF₃ H C₂H₅  52, 311, 570, H —OCF₃ H n-C₃H₇  53, 312, 571, H —OCF₃ H n-C₄H₉  54, 313, 572, H —OCF₃ H n-C₅H₁₁  55, 314, 573, H —OCF₃ H n-C₆H₁₃  56, 315, 574, H —OCF₃ H n-C₇H₁₅  57, 316, 575, H H CH₃ CH₃  58, 317, 576, H H CH₃ C₂H₅  59, 318, 577, H H CH₃ n-C₃H₇  60, 319, 578, H H CH₃ n-C₄H₉  61, 320, 579, H H CH₃ n-C₅H₁₁  62, 321, 580, H H CH₃ n-C₆H₁₃  63, 322, 581, H H CH₃ n-C₇H₁₅  64, 323, 582, F H CH₃ CH₃  65, 324, 583, F H CH₃ C₂H₅  66, 325, 584, F H CH₃ n-C₃H₇  67, 326, 585, F H CH₃ n-C₄H₉  68, 327, 586, F H CH₃ n-C₅H₁₁  69, 328, 587, F H CH₃ n-C₆H₁₃  70, 329, 588, F H CH₃ n-C₇H₁₅  71, 330, 589, F F CH₃ CH₃  72, 331, 590, F F CH₃ C₂H₅  73, 332, 591, F F CH₃ n-C₃H₇  74, 333, 592, F F CH₃ n-C₄H₉  75, 334, 593, F F CH₃ n-C₅H₁₁  76, 335, 594, F F CH₃ n-C₆H₁₃  77, 336, 595, F F CH₃ n-C₇H₁₅  78, 337, 596, CF₃ H CH₃ CH₃  79, 338, 597, CF₃ H CH₃ C₂H₅  80, 339, 598, CF₃ H CH₃ n-C₃H₇  81, 340, 599, CF₃ H CH₃ n-C₄H₉  82, 341, 600, CF₃ H CH₃ n-C₅H₁₁  83, 342, 601, CF₃ H CH₃ n-C₆H₁₃  84, 343, 602, CF₃ H CH₃ n-C₇H₁₅  85, 344, 603, —OCF₃ H CH₃ CH₃  86, 345, 604, —OCF₃ H CH₃ C₂H₅  87, 346, 605, —OCF₃ H CH₃ n-C₃H₇  88, 347, 606, —OCF₃ H CH₃ n-C₄H₉  89, 348, 607, —OCF₃ H CH₃ n-C₅H₁₁  90, 349, 608, —OCF₃ H CH₃ n-C₆H₁₃  91, 350, 609, —OCF₃ H CH₃ n-C₇H₁₅  92, 351, 610, H H C₂H₅ C₂H₅  93, 352, 611, H H C₂H₅ n-C₃H₇  94, 353, 612, H H C₂H₅ n-C₄H₉  95, 354, 613, H H C₂H₅ n-C₅H₁₁  96, 355, 614, H H C₂H₅ n-C₆H₁₃  97, 356, 615, H H C₂H₅ n-C₇H₁₅  98, 357, 616, F H C₂H₅ CH₃  99, 358, 617, F H C₂H₅ C₂H₅ 100, 359, 618, F H C₂H₅ n-C₃H₇ 101, 360, 619, F H C₂H₅ n-C₄H₉ 102, 361, 620, F H C₂H₅ n-C₅H₁₁ 103, 362, 621, F H C₂H₅ n-C₆H₁₃ 104, 363, 622, F H C₂H₅ n-C₇H₁₅ 105, 364, 623, F F C₂H₅ C₂H₅ 106, 365, 624, F F C₂H₅ n-C₃H₇ 107, 366, 625, F F C₂H₅ n-C₄H₉ 108, 367, 626, F F C₂H₅ n-C₅H₁₁ 109, 368, 627, F F C₂H₅ n-C₆H₁₃ 110, 369, 628, F F C₂H₅ n-C₇H₁₅ 111, 370, 629, CF₃ H C₂H₅ CH₃ 112, 371, 630, CF₃ H C₂H₅ C₂H₅ 113, 372, 631, CF₃ H C₂H₅ n-C₃H₇ 114, 373, 632, CF₃ H C₂H₅ n-C₄H₉ 115, 374, 633, CF₃ H C₂H₅ n-C₅H₁₁ 116, 375, 634, CF₃ H C₂H₅ n-C₆H₁₃ 117, 376, 635, CF₃ H C₂H₅ n-C₇H₁₅ 118, 377, 636, —OCF₃ H C₂H₅ CH₃ 119, 378, 637, —OCF₃ H C₂H₅ C₂H₅ 120, 379, 638, —OCF₃ H C₂H₅ n-C₃H₇ 121, 380, 639, —OCF₃ H C₂H₅ n-C₄H₉ 122, 381, 640, —OCF₃ H C₂H₅ n-C₅H₁₁ 123, 382, 641, —OCF₃ H C₂H₅ n-C₆H₁₃ 124, 383, 642, —OCF₃ H C₂H₅ n-C₇H₁₅ 125, 384, 643, H H n-C₃H₇ n-C₃H₇ 126, 385, 644, H H n-C₃H₇ n-C₄H₉ 127, 386, 645, H H n-C₃H₇ n-C₅H₁₁ 128, 387, 646, H H n-C₃H₇ n-C₆H₁₃ 129, 388, 647, H H n-C₃H₇ n-C₇H₁₅ 130, 389, 648, F H n-C₃H₇ CH₃ 131, 390, 649, F H n-C₃H₇ C₂H₅ 132, 391, 650, F H n-C₃H₇ n-C₃H₇ 133, 392, 651, F H n-C₃H₇ n-C₄H₉ 134, 393, 652, F H n-C₃H₇ n-C₅H₁₁ 135, 394, 653, F H n-C₃H₇ n-C₆H₁₃ 136, 395, 654, F H n-C₃H₇ n-C₇H₁₅ 137, 396, 655, F F n-C₃H₇ n-C₃H₇ 138, 397, 656, F F n-C₃H₇ n-C₄H₉ 139, 398, 657, F F n-C₃H₇ n-C₅H₁₁ 140, 399, 658, F F n-C₃H₇ n-C₆H₁₃ 141, 400, 659, F F n-C₃H₇ n-C₇H₁₅ 142, 401, 660, CF₃ H n-C₃H₇ CH₃ 143, 402, 661, CF₃ H n-C₃H₇ C₂H₅ 144, 403, 662, CF₃ H n-C₃H₇ n-C₃H₇ 145, 404, 663, CF₃ H n-C₃H₇ n-C₄H₉ 146, 405, 664, CF₃ H n-C₃H₇ n-C₅H₁₁ 147, 406, 665, CF₃ H n-C₃H₇ n-C₆H₁₃ 148, 407, 666, CF₃ H n-C₃H₇ n-C₇H₁₅ 149, 408, 667, —OCF₃ H n-C₃H₇ CH₃ 150, 409, 668, —OCF₃ H n-C₃H₇ C₂H₅ 151, 410, 669, —OCF₃ H n-C₃H₇ n-C₃H₇ 152, 411, 670, —OCF₃ H n-C₃H₇ n-C₄H₉ 153, 412, 671, —OCF₃ H n-C₃H₇ n-C₅H₁₁ 154, 413, 672, —OCF₃ H n-C₃H₇ n-C₆H₁₃ 155, 414, 673, —OCF₃ H n-C₃H₇ n-C₇H₁₅ 156, 415, 674, H H n-C₄H₉ n-C₄H₉ 157, 416, 675, H H n-C₄H₉ n-C₅H₁₁ 158, 417, 676, H H n-C₄H₉ n-C₆H₁₃ 159, 418, 677, H H n-C₄H₉ n-C₇H₁₅ 160, 419, 678, F H n-C₄H₉ CH₃ 161, 420, 679, F H n-C₄H₉ C₂H₅ 162, 421, 680, F H n-C₄H₉ n-C₃H₇ 163, 422, 681, F H n-C₄H₉ n-C₄H₉ 164, 423, 682, F H n-C₄H₉ n-C₅H₁₁ 165, 424, 683, F H n-C₄H₉ n-C₆H₁₃ 166, 425, 684, F H n-C₄H₉ n-C₇H₁₅ 167, 426, 685, F F n-C₄H₉ n-C₄H₉ 168, 427, 686, F F n-C₄H₉ n-C₅H₁₁ 169, 428, 687, F F n-C₄H₉ n-C₆H₁₃ 170, 429, 688, F F n-C₄H₉ n-C₇H₁₅ 171, 430, 689, CF₃ H n-C₄H₉ CH₃ 172, 431, 690, CF₃ H n-C₄H₉ C₂H₅ 173, 432, 691, CF₃ H n-C₄H₉ n-C₃H₇ 174, 433, 692, CF₃ H n-C₄H₉ n-C₄H₉ 175, 434, 693, CF₃ H n-C₄H₉ n-C₅H₁₁ 176, 435, 694, CF₃ H n-C₄H₉ n-C₆H₁₃ 177, 436, 695, CF₃ H n-C₄H₉ n-C₇H₁₅ 178, 437, 696, —OCF₃ H n-C₄H₉ CH₃ 179, 438, 697, —OCF₃ H n-C₄H₉ C₂H₅ 180, 439, 698, —OCF₃ H n-C₄H₉ n-C₃H₇ 181, 440, 699, —OCF₃ H n-C₄H₉ n-C₄H₉ 182, 441, 700, —OCF₃ H n-C₄H₉ n-C₅H₁₁ 183, 442, 701, —OCF₃ H n-C₄H₉ n-C₆H₁₃ 184, 443, 702, —OCF₃ H n-C₄H₉ n-C₇H₁₅ 185, 444, 703, H H n-C₅H₁₁ n-C₅H₁₁ 186, 445, 704, H H n-C₅H₁₁ n-C₆H₁₃ 187, 446, 705, H H n-C₅H₁₁ n-C₇H₁₅ 188, 447, 706, F H n-C₅H₁₁ CH₃ 189, 448, 707, F H n-C₅H₁₁ C₂H₅ 190, 449, 708, F H n-C₅H₁₁ n-C₃H₇ 191, 450, 709, F H n-C₅H₁₁ n-C₄H₉ 192, 451, 710, F H n-C₅H₁₁ n-C₅H₁₁ 193, 452, 711, F H n-C₅H₁₁ n-C₆H₁₃ 194, 453, 712, F H n-C₅H₁₁ n-C₇H₁₅ 195, 454, 713, F F n-C₅H₁₁ n-C₅H₁₁ 196, 455, 714, F F n-C₅H₁₁ n-C₆H₁₃ 197, 456, 715, F F n-C₅H₁₁ n-C₇H₁₅ 198, 457, 716, CF₃ H n-C₅H₁₁ CH₃ 199, 458, 717, CF₃ H n-C₅H₁₁ C₂H₅ 200, 459, 718, CF₃ H n-C₅H₁₁ n-C₃H₇ 201, 460, 719, CF₃ H n-C₅H₁₁ n-C₄H₉ 202, 461, 720, CF₃ H n-C₅H₁₁ n-C₅H₁₁ 203, 462, 721, CF₃ H n-C₅H₁₁ n-C₆H₁₃ 204, 463, 722, CF₃ H n-C₅H₁₁ n-C₇H₁₅ 205, 464, 723, —OCF₃ H n-C₅H₁₁ CH₃ 206, 465, 724, —OCF₃ H n-C₅H₁₁ C₂H₅ 207, 466, 725, —OCF₃ H n-C₅H₁₁ n-C₃H₇ 208, 467, 726, —OCF₃ H n-C₅H₁₁ n-C₄H₉ 209, 468, 727, —OCF₃ H n-C₅H₁₁ n-C₅H₁₁ 210, 469, 728, —OCF₃ H n-C₅H₁₁ n-C₆H₁₃ 211, 470, 729, —OCF₃ H n-C₅H₁₁ n-C₇H₁₅ 212, 471, 730, H H n-C₆H₁₃ n-C₆H₁₃ 213, 472, 731, H H n-C₆H₁₃ n-C₇H₁₅ 214, 473, 732, F H n-C₆H₁₃ CH₃ 215, 474, 733, F H n-C₆H₁₃ C₂H₅ 216, 475, 734, F H n-C₆H₁₃ n-C₃H₇ 217, 476, 735, F H n-C₆H₁₃ n-C₄H₉ 218, 477, 736, F H n-C₆H₁₃ n-C₅H₁₁ 219, 478, 737, F H n-C₆H₁₃ n-C₆H₁₃ 220, 479, 738, F H n-C₆H₁₃ n-C₇H₁₅ 221, 480, 739, F F n-C₆H₁₃ n-C₆H₁₃ 222, 481, 740, F F n-C₆H₁₃ n-C₇H₁₅ 223, 482, 741, CF₃ H n-C₆H₁₃ CH₃ 224, 483, 742, CF₃ H n-C₆H₁₃ C₂H₅ 225, 484, 743, CF₃ H n-C₆H₁₃ n-C₃H₇ 226, 485, 744, CF₃ H n-C₆H₁₃ n-C₄H₉ 227, 486, 745, CF₃ H n-C₆H₁₃ n-C₅H₁₁ 228, 487, 746, CF₃ H n-C₆H₁₃ n-C₆H₁₃ 229, 488, 747, CF₃ H n-C₆H₁₃ n-C₇H₁₅ 230, 489, 748, —OCF₃ H n-C₆H₁₃ CH₃ 231, 490, 749, —OCF₃ H n-C₆H₁₃ C₂H₅ 232, 491, 750, —OCF₃ H n-C₆H₁₃ n-C₃H₇ 233, 492, 751, —OCF₃ H n-C₆H₁₃ n-C₄H₉ 234, 493, 752, —OCF₃ H n-C₆H₁₃ n-C₅H₁₁ 235, 494, 753, —OCF₃ H n-C₆H₁₃ n-C₆H₁₃ 236, 495, 754, —OCF₃ H n-C₆H₁₃ n-C₇H₁₅ 237, 496, 755, H H n-C₇H₁₅ n-C₇H₁₅ 238, 497, 756, F H n-C₇H₁₅ CH₃ 239, 498, 757, F H n-C₇H₁₅ C₂H₅ 240, 499, 758, F H n-C₇H₁₅ n-C₃H₇ 241, 500, 759, F H n-C₇H₁₅ n-C₄H₉ 242, 501, 760, F H n-C₇H₁₅ n-C₅H₁₁ 243, 502, 761, F H n-C₇H₁₅ n-C₆H₁₃ 244, 503, 762, F H n-C₇H₁₅ n-C₇H₁₅ 245, 504, 763, F F n-C₇H₁₅ n-C₇H₁₅ 246, 505, 764, CF₃ H n-C₇H₁₅ CH₃ 247, 506, 765, CF₃ H n-C₇H₁₅ C₂H₅ 248, 507, 766, CF₃ H n-C₇H₁₅ n-C₃H₇ 249, 508, 767, CF₃ H n-C₇H₁₅ n-C₄H₉ 250, 509, 768, CF₃ H n-C₇H₁₅ n-C₅H₁₁ 251, 510, 769, CF₃ H n-C₇H₁₅ n-C₆H₁₃ 252, 511, 770, CF₃ H n-C₇H₁₅ n-C₇H₁₅ 253, 512, 771, —OCF₃ H n-C₇H₁₅ CH₃ 254, 513, 772, —OCF₃ H n-C₇H₁₅ C₂H₅ 255, 514, 773, —OCF₃ H n-C₇H₁₅ n-C₃H₇ 256, 515, 774, —OCF₃ H n-C₇H₁₅ n-C₄H₉ 257, 516, 775, —OCF₃ H n-C₇H₁₅ n-C₅H₁₁ 258, 517, 776, —OCF₃ H n-C₇H₁₅ n-C₆H₁₃ 259, 518, 777, —OCF₃ H n-C₇H₁₅ n-C₇H₁₅

Examples 778-840

Examples 841-903

Examples 904-966

Examples 967-1029

Example No. R¹ R² 778, 841, 904, 967, H CH₃ 779, 842, 905, 968, H C₂H₅ 780, 843, 906, 969, H n-C₃H₇ 781, 844, 907, 970, H n-C₄H₉ 782, 845, 908, 971, H n-C₅H₁₁ 783, 846, 909, 972, H n-C₆H₁₃ 784, 847, 910, 973, H n-C₇H₁₅ 785, 848, 911, 974, CH₃ H 786, 849, 912, 975, CH₃ CH₃ 787, 850, 913, 976, CH₃ C₂H₅ 788, 851, 914, 977, CH₃ n-C₃H₇ 789, 852, 915, 978, CH₃ n-C₄H₉ 790, 853, 916, 979, CH₃ n-C₅H₁₁ 791, 854, 917, 980, CH₃ n-C₆H₁₃ 792, 855, 918, 981, CH₃ n-C₇H₁₅ 793, 856, 919, 982, C₂H₅ H 794, 857, 920, 983, C₂H₅ CH₃ 795, 858, 921, 984, C₂H₅ C₂H₅ 796, 859, 922, 985, C₂H₅ n-C₃H₇ 797, 860, 923, 986, C₂H₅ n-C₄H₉ 798, 861, 924, 987, C₂H₅ n-C₅H₁₁ 799, 862, 925, 988, C₂H₅ n-C₆H₁₃ 800, 863, 926, 989, C₂H₅ n-C₇H₁₅ 801, 864, 927, 990, n-C₃H₇ H 802, 865, 928, 991, n-C₃H₇ CH₃ 803, 866, 929, 992, n-C₃H₇ C₂H₅ 804, 867, 930, 993, n-C₃H₇ n-C₃H₇ 805, 868, 931, 994, n-C₃H₇ n-C₄H₉ 806, 869, 932, 995, n-C₃H₇ n-C₅H₁₁ 807, 870, 933, 996, n-C₃H₇ n-C₆H₁₃ 808, 871, 934, 997, n-C₃H₇ n-C₇H₁₅ 809, 872, 935, 998, n-C₄H₉ H 810, 873, 936, 999, n-C₄H₉ CH₃ 811, 874, 937, 1000, n-C₄H₉ C₂H₅ 812, 875, 938, 1001, n-C₄H₉ n-C₃H₇ 813, 876, 939, 1002, n-C₄H₉ n-C₄H₉ 814, 877, 940, 1003, n-C₄H₉ n-C₅H₁₁ 815, 878, 941, 1004, n-C₄H₉ n-C₆H₁₃ 816, 879, 942, 1005, n-C₄H₉ n-C₇H₁₅ 817, 880, 943, 1006, n-C₅H₁₁ H 818, 881, 944, 1007, n-C₅H₁₁ CH₃ 819, 882, 945, 1008, n-C₅H₁₁ C₂H₅ 820, 883, 946, 1009, n-C₅H₁₁ n-C₃H₇ 821, 884, 947, 1010, n-C₅H₁₁ n-C₄H₉ 822, 885, 948, 1011, n-C₅H₁₁ n-C₅H₁₁ 823, 886, 949, 1012, n-C₅H₁₁ n-C₆H₁₃ 824, 887, 950, 1013, n-C₅H₁₁ n-C₇H₁₅ 825, 888, 951, 1014, n-C₆H₁₃ H 826, 889, 952, 1015, n-C₆H₁₃ CH₃ 827, 890, 953, 1016, n-C₆H₁₃ C₂H₅ 828, 891, 954, 1017, n-C₆H₁₃ n-C₃H₇ 829, 892, 955, 1018, n-C₆H₁₃ n-C₄H₉ 830, 893, 956, 1019, n-C₆H₁₃ n-C₅H₁₁ 831, 894, 957, 1020, n-C₆H₁₃ n-C₆H₁₃ 832, 895, 958, 1021, n-C₆H₁₃ n-C₇H₁₅ 833, 896, 959, 1022, n-C₇H₁₅ H 834, 897, 960, 1023, n-C₇H₁₅ CH₃ 835, 898, 961, 1024, n-C₇H₁₅ C₂H₅ 836, 899, 962, 1025, n-C₇H₁₅ n-C₃H₇ 837, 900, 963, 1026, n-C₇H₁₅ n-C₄H₉ 838, 901, 964, 1027, n-C₇H₁₅ n-C₅H₁₁ 839, 902, 965, 1028, n-C₇H₁₅ n-C₆H₁₃ 840, 903, 966, 1029, n-C₇H₁₅ n-C₇H₁₅

Examples 1030-1142

Examples 1143-1255

Examples 1256-1368

Examples 1369-1481

Example No. R¹ R² Z 1030, 1143, 1256, 1369, CH₃ H bond 1031, 1144, 1257, 1370, CH₃ CH₃ bond 1032, 1145, 1258, 1371, CH₃ C₂H₅ bond 1033, 1146, 1259, 1372, CH₃ n-C₃H₇ bond 1034, 1147, 1260, 1373, CH₃ n-C₄H₉ bond 1035, 1148, 1261, 1374, CH₃ n-C₅H₁₁ bond 1036, 1149, 1262, 1375, CH₃ n-C₆H₁₃ bond 1037, 1150, 1263, 1376, CH₃ n-C₇H₁₅ bond 1038, 1151, 1264, 1377, CH₃ H CF₂CF₂ 1039, 1152, 1265, 1378, CH₃ CH₃ CF₂CF₂ 1040, 1153, 1266, 1379, CH₃ C₂H₅ CF₂CF₂ 1041, 1154, 1267, 1380, CH₃ n-C₃H₇ CF₂CF₂ 1042, 1155, 1268, 1381, CH₃ n-C₄H₉ CF₂CF₂ 1043, 1156, 1269, 1382, CH₃ n-C₅H₁₁ CF₂CF₂ 1044, 1157, 1270, 1383, CH₃ n-C₆H₁₃ CF₂CF₂ 1045, 1158, 1271, 1384, CH₃ n-C₇H₁₅ CF₂CF₂ 1046, 1159, 1272, 1385, C₂H₅ H bond 1047, 1160, 1273, 1386, C₂H₅ CH₃ bond 1048, 1161, 1274, 1387, C₂H₅ C₂H₅ bond 1049, 1162, 1275, 1388, C₂H₅ n-C₃H₇ bond 1050, 1163, 1276, 1389, C₂H₅ n-C₄H₉ bond 1051, 1164, 1277, 1390, C₂H₅ n-C₅H₁₁ bond 1052, 1165, 1278, 1391, C₂H₅ n-C₆H₁₃ bond 1053, 1166, 1279, 1392, C₂H₅ n-C₇H₁₅ bond 1054, 1167, 1280, 1393, C₂H₅ H CF₂CF₂ 1055, 1168, 1281, 1394, C₂H₅ CH₃ CF₂CF₂ 1056, 1169, 1282, 1395, C₂H₅ C₂H₅ CF₂CF₂ 1057, 1170, 1283, 1396, C₂H₅ n-C₃H₇ CF₂CF₂ 1058, 1171, 1284, 1397, C₂H₅ n-C₄H₉ CF₂CF₂ 1059, 1172, 1285, 1398, C₂H₅ n-C₅H₁₁ CF₂CF₂ 1060, 1173, 1286, 1399, C₂H₅ n-C₆H₁₃ CF₂CF₂ 1061, 1174, 1287, 1400, C₂H₅ n-C₇H₁₅ CF₂CF₂ 1062, 1175, 1288, 1401, n-C₃H₇ H bond 1063, 1176, 1289, 1402, n-C₃H₇ CH₃ bond 1064, 1177, 1290, 1403, n-C₃H₇ C₂H₅ bond 1065, 1178, 1291, 1404, n-C₃H₇ n-C₃H₇ bond 1066, 1179, 1292, 1405, n-C₃H₇ n-C₄H₉ bond 1067, 1180, 1293, 1406, n-C₃H₇ n-C₅H₁₁ bond 1068, 1181, 1294, 1407, n-C₃H₇ n-C₆H₁₃ bond 1069, 1182, 1295, 1408, n-C₃H₇ n-C₇H₁₅ bond 1070, 1183, 1296, 1409, n-C₃H₇ H CF₂CF₂ 1071, 1184, 1297, 1410, n-C₃H₇ CH₃ CF₂CF₂ 1072, 1185, 1298, 1411, n-C₃H₇ C₂H₅ CF₂CF₂ 1073, 1186, 1299, 1412, n-C₃H₇ n-C₃H₇ CF₂CF₂ 1074, 1187, 1300, 1413, n-C₃H₇ n-C₄H₉ CF₂CF₂ 1075, 1188, 1301, 1414, n-C₃H₇ n-C₅H₁₁ CF₂CF₂ 1076, 1189, 1302, 1415, n-C₃H₇ n-C₆H₁₃ CF₂CF₂ 1077, 1190, 1303, 1416, n-C₃H₇ n-C₇H₁₅ CF₂CF₂ 1078, 1191, 1304, 1417, n-C₄H₉ H bond 1079, 1192, 1305, 1418, n-C₄H₉ CH₃ bond 1080, 1193, 1306, 1419, n-C₄H₉ C₂H₅ bond 1081, 1194, 1307, 1420, n-C₄H₉ n-C₃H₇ bond 1082, 1195, 1308, 1421, n-C₄H₉ n-C₄H₉ bond 1083, 1196, 1309, 1422, n-C₄H₉ n-C₅H₁₁ bond 1084, 1197, 1310, 1423, n-C₄H₉ n-C₆H₁₃ bond 1085, 1198, 1311, 1424, n-C₄H₉ n-C₇H₁₅ bond 1086, 1199, 1312, 1425, n-C₄H₉ H CF₂CF₂ 1087, 1200, 1313, 1426, n-C₄H₉ CH₃ CF₂CF₂ 1088, 1201, 1314, 1427, n-C₄H₉ C₂H₅ CF₂CF₂ 1089, 1202, 1315, 1428, n-C₄H₉ n-C₃H₇ CF₂CF₂ 1090, 1203, 1316, 1429, n-C₄H₉ n-C₄H₉ CF₂CF₂ 1091, 1204, 1317, 1430, n-C₄H₉ n-C₅H₁₁ CF₂CF₂ 1092, 1205, 1318, 1431, n-C₄H₉ n-C₆H₁₃ CF₂CF₂ 1093, 1206, 1319, 1432, n-C₄H₉ n-C₇H₁₅ CF₂CF₂ 1094, 1207, 1320, 1433, n-C₅H₁₁ n-C₇H₁₅ bond 1095, 1208, 1321, 1434, n-C₅H₁₁ H bond 1096, 1209, 1322, 1435, n-C₅H₁₁ CH₃ bond 1097, 1210, 1323, 1436, n-C₅H₁₁ C₂H₅ bond 1098, 1211, 1324, 1437, n-C₅H₁₁ n-C₃H₇ bond 1099, 1212, 1325, 1438, n-C₅H₁₁ n-C₄H₉ bond 1100, 1213, 1326, 1439, n-C₅H₁₁ n-C₅H₁₁ bond 1101, 1214, 1327, 1440, n-C₅H₁₁ n-C₆H₁₃ bond 1102, 1215, 1328, 1441, n-C₅H₁₁ n-C₇H₁₅ bond 1103, 1216, 1329, 1442, n-C₅H₁₁ H CF₂CF₂ 1104, 1217, 1330, 1443, n-C₅H₁₁ CH₃ CF₂CF₂ 1105, 1218, 1331, 1444, n-C₅H₁₁ C₂H₅ CF₂CF₂ 1106, 1219, 1332, 1445, n-C₅H₁₁ n-C₃H₇ CF₂CF₂ 1107, 1220, 1333, 1446, n-C₅H₁₁ n-C₄H₉ CF₂CF₂ 1108, 1221, 1334, 1447, n-C₅H₁₁ n-C₅H₁₁ CF₂CF₂ 1109, 1222, 1335, 1448, n-C₅H₁₁ n-C₆H₁₃ CF₂CF₂ 1110, 1223, 1336, 1449, n-C₅H₁₁ n-C₇H₁₅ CF₂CF₂ 1111, 1224, 1337, 1450, n-C₆H₁₃ H bond 1112, 1225, 1338, 1451, n-C₆H₁₃ CH₃ bond 1113, 1226, 1339, 1452, n-C₆H₁₃ C₂H₅ bond 1114, 1227, 1340, 1453, n-C₆H₁₃ n-C₃H₇ bond 1115, 1228, 1341, 1454, n-C₆H₁₃ n-C₄H₉ bond 1116, 1229, 1342, 1455, n-C₆H₁₃ n-C₅H₁₁ bond 1117, 1230, 1343, 1456, n-C₆H₁₃ n-C₆H₁₃ bond 1118, 1231, 1344, 1457, n-C₆H₁₃ n-C₇H₁₅ bond 1119, 1232, 1345, 1458, n-C₆H₁₃ H CF₂CF₂ 1120, 1233, 1346, 1459, n-C₆H₁₃ CH₃ CF₂CF₂ 1121, 1234, 1347, 1460, n-C₆H₁₃ C₂H₅ CF₂CF₂ 1122, 1235, 1348, 1461, n-C₆H₁₃ n-C₃H₇ CF₂CF₂ 1123, 1236, 1349, 1462, n-C₆H₁₃ n-C₄H₉ CF₂CF₂ 1124, 1237, 1350, 1463, n-C₆H₁₃ n-C₅H₁₁ CF₂CF₂ 1125, 1238, 1351, 1464, n-C₆H₁₃ n-C₆H₁₃ CF₂CF₂ 1126, 1239, 1352, 1465, n-C₆H₁₃ n-C₇H₁₅ CF₂CF₂ 1127, 1240, 1353, 1466, n-C₇H₁₅ H bond 1128, 1241, 1354, 1467, n-C₇H₁₅ CH₃ bond 1129, 1242, 1355, 1468, n-C₇H₁₅ C₂H₅ bond 1130, 1243, 1356, 1469, n-C₇H₁₅ n-C₃H₇ bond 1131, 1244, 1357, 1470, n-C₇H₁₅ n-C₄H₉ bond 1132, 1245, 1358, 1471, n-C₇H₁₅ n-C₅H₁₁ bond 1133, 1246, 1359, 1472, n-C₇H₁₅ n-C₆H₁₃ bond 1134, 1247, 1360, 1473, n-C₇H₁₅ n-C₇H₁₅ bond 1135, 1248, 1361, 1474, n-C₇H₁₅ H CF₂CF₂ 1136, 1249, 1362, 1475, n-C₇H₁₅ CH₃ CF₂CF₂ 1137, 1250, 1363, 1476, n-C₇H₁₅ C₂H₅ CF₂CF₂ 1138, 1251, 1364, 1477, n-C₇H₁₅ n-C₃H₇ CF₂CF₂ 1139, 1252, 1365, 1478, n-C₇H₁₅ n-C₄H₉ CF₂CF₂ 1140, 1253, 1366, 1479, n-C₇H₁₅ n-C₅H₁₁ CF₂CF₂ 1141, 1254, 1367, 1480, n-C₇H₁₅ n-C₆H₁₃ CF₂CF₂ 1142, 1255, 1368, 1481, n-C₇H₁₅ n-C₇H₁₅ CF₂CF₂

Examples 1482-1594

Examples 1595-1707

Examples 1708-1820

Examples 1821-1933

Example No. R¹ R² Z 1482, 1595, 1708, 1821, CH₃ H bond 1483, 1596, 1709, 1822, CH₃ CH₃ bond 1484, 1597, 1710, 1823, CH₃ C₂H₅ bond 1485, 1598, 1711, 1824, CH₃ n-C₃H₇ bond 1486, 1599, 1712, 1825, CH₃ n-C₄H₉ bond 1487, 1600, 1713, 1826, CH₃ n-C₅H₁₁ bond 1488, 1601, 1714, 1827, CH₃ n-C₆H₁₃ bond 1489, 1602, 1715, 1828, CH₃ n-C₇H₁₅ bond 1490, 1603, 1716, 1829, CH₃ H CF₂CF₂ 1491, 1604, 1717, 1830, CH₃ CH₃ CF₂CF₂ 1492, 1605, 1718, 1831, CH₃ C₂H₅ CF₂CF₂ 1493, 1606, 1719, 1832, CH₃ n-C₃H₇ CF₂CF₂ 1494, 1607, 1720, 1833, CH₃ n-C₄H₉ CF₂CF₂ 1495, 1608, 1721, 1834, CH₃ n-C₅H₁₁ CF₂CF₂ 1496, 1609, 1722, 1835, CH₃ n-C₆H₁₃ CF₂CF₂ 1497, 1610, 1723, 1836, CH₃ n-C₇H₁₅ CF₂CF₂ 1498, 1611, 1724, 1837, C₂H₅ H bond 1499, 1612, 1725, 1838, C₂H₅ CH₃ bond 1500, 1613, 1726, 1839, C₂H₅ C₂H₅ bond 1501, 1614, 1727, 1840, C₂H₅ n-C₃H₇ bond 1502, 1615, 1728, 1841, C₂H₅ n-C₄H₉ bond 1503, 1616, 1729, 1842, C₂H₅ n-C₅H₁₁ bond 1504, 1617, 1730, 1843, C₂H₅ n-C₆H₁₃ bond 1505, 1618, 1731, 1844, C₂H₅ n-C₇H₁₅ bond 1506, 1619, 1732, 1845, C₂H₅ H CF₂CF₂ 1507, 1620, 1733, 1846, C₂H₅ CH₃ CF₂CF₂ 1508, 1621, 1734, 1847, C₂H₅ C₂H₅ CF₂CF₂ 1509, 1622, 1735, 1848, C₂H₅ n-C₃H₇ CF₂CF₂ 1510, 1623, 1736, 1849, C₂H₅ n-C₄H₉ CF₂CF₂ 1511, 1624, 1737, 1850, C₂H₅ n-C₅H₁₁ CF₂CF₂ 1512, 1625, 1738, 1851, C₂H₅ n-C₆H₁₃ CF₂CF₂ 1513, 1626, 1739, 1852, C₂H₅ n-C₇H₁₅ CF₂CF₂ 1514, 1627, 1740, 1853, n-C₃H₇ H bond 1515, 1628, 1741, 1854, n-C₃H₇ CH₃ bond 1516, 1629, 1742, 1855, n-C₃H₇ C₂H₅ bond 1517, 1630, 1743, 1856, n-C₃H₇ n-C₃H₇ bond 1518, 1631, 1744, 1857, n-C₃H₇ n-C₄H₉ bond 1519, 1632, 1745, 1858, n-C₃H₇ n-C₅H₁₁ bond 1520, 1633, 1746, 1859, n-C₃H₇ n-C₆H₁₃ bond 1521, 1634, 1747, 1860, n-C₃H₇ n-C₇H₁₅ bond 1522, 1635, 1748, 1861, n-C₃H₇ H CF₂CF₂ 1523, 1636, 1749, 1862, n-C₃H₇ CH₃ CF₂CF₂ 1524, 1637, 1750, 1863, n-C₃H₇ C₂H₅ CF₂CF₂ 1525, 1638, 1751, 1864, n-C₃H₇ n-C₃H₇ CF₂CF₂ 1526, 1639, 1752, 1865, n-C₃H₇ n-C₄H₉ CF₂CF₂ 1527, 1640, 1753, 1866, n-C₃H₇ n-C₅H₁₁ CF₂CF₂ 1528, 1641, 1754, 1867, n-C₃H₇ n-C₆H₁₃ CF₂CF₂ 1529, 1642, 1755, 1868, n-C₃H₇ n-C₇H₁₅ CF₂CF₂ 1530, 1643, 1756, 1869, n-C₄H₉ H bond 1531, 1644, 1757, 1870, n-C₄H₉ CH₃ bond 1532, 1645, 1758, 1871, n-C₄H₉ C₂H₅ bond 1533, 1646, 1759, 1872, n-C₄H₉ n-C₃H₇ bond 1534, 1647, 1760, 1873, n-C₄H₉ n-C₄H₉ bond 1535, 1648, 1761, 1874, n-C₄H₉ n-C₅H₁₁ bond 1536, 1649, 1762, 1875, n-C₄H₉ n-C₆H₁₃ bond 1537, 1650, 1763, 1876, n-C₄H₉ n-C₇H₁₅ bond 1538, 1651, 1764, 1877, n-C₄H₉ H CF₂CF₂ 1539, 1652, 1765, 1878, n-C₄H₉ CH₃ CF₂CF₂ 1540, 1653, 1766, 1879, n-C₄H₉ C₂H₅ CF₂CF₂ 1541, 1654, 1767, 1880, n-C₄H₉ n-C₃H₇ CF₂CF₂ 1542, 1655, 1768, 1881, n-C₄H₉ n-C₄H₉ CF₂CF₂ 1543, 1656, 1769, 1882, n-C₄H₉ n-C₅H₁₁ CF₂CF₂ 1544, 1657, 1770, 1883, n-C₄H₉ n-C₆H₁₃ CF₂CF₂ 1545, 1658, 1771, 1884, n-C₄H₉ n-C₇H₁₅ CF₂CF₂ 1546, 1659, 1772, 1885, n-C₅H₁₁ n-C₇H₁₅ bond 1547, 1660, 1773, 1886, n-C₅H₁₁ H bond 1548, 1661, 1774, 1887, n-C₅H₁₁ CH₃ bond 1549, 1662, 1775, 1888, n-C₅H₁₁ C₂H₅ bond 1550, 1663, 1776, 1889, n-C₅H₁₁ n-C₃H₇ bond 1551, 1664, 1777, 1890, n-C₅H₁₁ n-C₄H₉ bond 1552, 1665, 1778, 1891, n-C₅H₁₁ n-C₅H₁₁ bond 1553, 1666, 1779, 1892, n-C₅H₁₁ n-C₆H₁₃ bond 1554, 1667, 1780, 1893, n-C₅H₁₁ n-C₇H₁₅ bond 1555, 1668, 1781, 1894, n-C₅H₁₁ H CF₂CF₂ 1556, 1669, 1782, 1895, n-C₅H₁₁ CH₃ CF₂CF₂ 1557, 1670, 1783, 1896, n-C₅H₁₁ C₂H₅ CF₂CF₂ 1558, 1671, 1784, 1897, n-C₅H₁₁ n-C₃H₇ CF₂CF₂ 1559, 1672, 1785, 1898, n-C₅H₁₁ n-C₄H₉ CF₂CF₂ 1560, 1673, 1786, 1899, n-C₅H₁₁ n-C₅H₁₁ CF₂CF₂ 1561, 1674, 1787, 1900, n-C₅H₁₁ n-C₆H₁₃ CF₂CF₂ 1562, 1675, 1788, 1901, n-C₅H₁₁ n-C₇H₁₅ CF₂CF₂ 1563, 1676, 1789, 1902, n-C₆H₁₃ H bond 1564, 1677, 1790, 1903, n-C₆H₁₃ CH₃ bond 1565, 1678, 1791, 1904, n-C₆H₁₃ C₂H₅ bond 1566, 1679, 1792, 1905, n-C₆H₁₃ n-C₃H₇ bond 1567, 1680, 1793, 1906, n-C₆H₁₃ n-C₄H₉ bond 1568, 1681, 1794, 1907, n-C₆H₁₃ n-C₅H₁₁ bond 1569, 1682, 1795, 1908, n-C₆H₁₃ n-C₆H₁₃ bond 1570, 1683, 1796, 1909, n-C₆H₁₃ n-C₇H₁₅ bond 1571, 1684, 1797, 1910, n-C₆H₁₃ H CF₂CF₂ 1572, 1685, 1798, 1911, n-C₆H₁₃ CH₃ CF₂CF₂ 1573, 1686, 1799, 1912, n-C₆H₁₃ C₂H₅ CF₂CF₂ 1574, 1687, 1800, 1913, n-C₆H₁₃ n-C₃H₇ CF₂CF₂ 1575, 1688, 1801, 1914, n-C₆H₁₃ n-C₄H₉ CF₂CF₂ 1576, 1689, 1802, 1915, n-C₆H₁₃ n-C₅H₁₁ CF₂CF₂ 1577, 1690, 1803, 1916, n-C₆H₁₃ n-C₆H₁₃ CF₂CF₂ 1578, 1691, 1804, 1917, n-C₆H₁₃ n-C₇H₁₅ CF₂CF₂ 1579, 1692, 1805, 1918, n-C₇H₁₅ H bond 1580, 1693, 1806, 1919, n-C₇H₁₅ CH₃ bond 1581, 1694, 1807, 1920, n-C₇H₁₅ C₂H₅ bond 1582, 1695, 1808, 1921, n-C₇H₁₅ n-C₃H₇ bond 1583, 1696, 1809, 1922, n-C₇H₁₅ n-C₄H₉ bond 1584, 1697, 1810, 1923, n-C₇H₁₅ n-C₅H₁₁ bond 1585, 1698, 1811, 1924, n-C₇H₁₅ n-C₆H₁₃ bond 1586, 1699, 1812, 1925, n-C₇H₁₅ n-C₇H₁₅ bond 1587, 1700, 1813, 1926, n-C₇H₁₅ H CF₂CF₂ 1588, 1701, 1814, 1927, n-C₇H₁₅ CH₃ CF₂CF₂ 1589, 1702, 1815, 1928, n-C₇H₁₅ C₂H₅ CF₂CF₂ 1590, 1703, 1816, 1929, n-C₇H₁₅ n-C₃H₇ CF₂CF₂ 1591, 1704, 1817, 1930, n-C₇H₁₅ n-C₄H₉ CF₂CF₂ 1592, 1705, 1818, 1931, n-C₇H₁₅ n-C₅H₁₁ CF₂CF₂ 1593, 1706, 1819, 1932, n-C₇H₁₅ n-C₆H₁₃ CF₂CF₂ 1594, 1707, 1820, 1933, n-C₇H₁₅ n-C₇H₁₅ CF₂CF₂

Examples 1934-1958

Examples 1959-1983

Examples 1984-2008

Examples 2009-2033

Example No. L¹ L² R² 1934, 1959, 1984, 2009, H H H 1935, 1960, 1985, 2010, F H H 1936, 1961, 1986, 2011, F F H 1937, 1962, 1987, 2012, F F H 1938, 1963, 1988, 2013, H H CH₃ 1939, 1964, 1989, 2014, F H CH₃ 1940, 1965, 1990, 2015, F F CH₃ 1941, 1966, 1991, 2016, H H C₂H₅ 1942, 1967, 1992, 2017, F H C₂H₅ 1943, 1968, 1993, 2018, F F C₂H₅ 1944, 1969, 1994, 2019, H H n-C₃H₇ 1945, 1970, 1995, 2020, F H n-C₃H₇ 1946, 1971, 1996, 2021, F F n-C₃H₇ 1947, 1972, 1997, 2022, H H n-C₄H₉ 1948, 1973, 1998, 2023, F H n-C₄H₉ 1949, 1974, 1999, 2024, F F n-C₄H₉ 1950, 1975, 2000, 2025, H H n-C₅H₁₁ 1951, 1976, 2001, 2026, F H n-C₅H₁₁ 1952, 1977, 2002, 2027, F F n-C₅H₁₁ 1953, 1978, 2003, 2028, H H n-C₆H₁₃ 1954, 1979, 2004, 2029, F H n-C₆H₁₃ 1955, 1980, 2005, 2030, F F n-C₆H₁₃ 1956, 1981, 2006, 2031, H H n-C₇H₁₅ 1957, 1982, 2007, 2032, F H n-C₇H₁₅ 1958, 1983, 2008, 2033, F F n-C₇H₁₅

Examples 2034-2058

Examples 2059-2083

Examples 2084-2108

Examples 2109-2133

Example No. L¹ L² R² 2034, 2059, 2084, 2109, H H H 2035, 2060, 2085, 2110, F H H 2036, 2061, 2086, 2111, F F H 2037, 2062, 2087, 2112, F F H 2038, 2063, 2088, 2113, H H CH₃ 2039, 2064, 2089, 2114, F H CH₃ 2040, 2065, 2090, 2115, F F CH₃ 2041, 2066, 2091, 2116, H H C₂H₅ 2042, 2067, 2092, 2117, F H C₂H₅ 2043, 2068, 2093, 2118, F F C₂H₅ 2044, 2069, 2094, 2119, H H n-C₃H₇ 2045, 2070, 2095, 2120, F H n-C₃H₇ 2046, 2071, 2096, 2121, F F n-C₃H₇ 2047, 2072, 2097, 2122, H H n-C₄H₉ 2048, 2073, 2098, 2123, F H n-C₄H₉ 2049, 2074, 2099, 2124, F F n-C₄H₉ 2050, 2075, 2100, 2125, H H n-C₅H₁₁ 2051, 2076, 2101, 2126, F H n-C₅H₁₁ 2052, 2077, 2102, 2127, F F n-C₅H₁₁ 2053, 2078, 2103, 2128, H H n-C₆H₁₃ 2054, 2079, 2104, 2129, F H n-C₆H₁₃ 2055, 2080, 2105, 2130, F F n-C₆H₁₃ 2056, 2081, 2106, 2131, H H n-C₇H₁₅ 2057, 2082, 2107, 2132, F H n-C₇H₁₅ 2058, 2083, 2108, 2133, F F n-C₇H₁₅

Examples 2134-2189

Examples 2190-2245

Examples 2246-2301

Examples 2302-2357

Example No. R² R³ 2134, 2190, 2246, 2302, H CH₃ 2135, 2191, 2247, 2303, H C₂H₅ 2136, 2192, 2248, 2304, H n-C₃H₇ 2137, 2193, 2249, 2305, H n-C₄H₉ 2138, 2194, 2250, 2306, H n-C₅H₁₁ 2139, 2195, 2251, 2307, H n-C₆H₁₃ 2140, 2196, 2252, 2308, H n-C₇H₁₅ 2141, 2197, 2253, 2309, CH₃ CH₃ 2142, 2198, 2254, 2310, CH₃ C₂H₅ 2143, 2199, 2255, 2311, CH₃ n-C₃H₇ 2144, 2200, 2256, 2312, CH₃ n-C₄H₉ 2145, 2201, 2257, 2313, CH₃ n-C₅H₁₁ 2146, 2202, 2258, 2314, CH₃ n-C₆H₁₃ 2147, 2203, 2259, 2315, CH₃ n-C₇H₁₅ 2148, 2204, 2260, 2316, C₂H₅ CH₃ 2149, 2205, 2261, 2317, C₂H₅ C₂H₅ 2150, 2206, 2262, 2318, C₂H₅ n-C₃H₇ 2151, 2207, 2263, 2319, C₂H₅ n-C₄H₉ 2152, 2208, 2264, 2320, C₂H₅ n-C₅H₁₁ 2153, 2209, 2265, 2321, C₂H₅ n-C₆H₁₃ 2154, 2210, 2266, 2322, C₂H₅ n-C₇H₁₅ 2155, 2211, 2267, 2323, n-C₃H₇ CH₃ 2156, 2212, 2268, 2324, n-C₃H₇ C₂H₅ 2157, 2213, 2269, 2325, n-C₃H₇ n-C₃H₇ 2158, 2214, 2270, 2326, n-C₃H₇ n-C₄H₉ 2159, 2215, 2271, 2327, n-C₃H₇ n-C₅H₁₁ 2160, 2216, 2272, 2328, n-C₃H₇ n-C₆H₁₃ 2161, 2217, 2273, 2329, n-C₃H₇ n-C₇H₁₅ 2162, 2218, 2274, 2330, n-C₄H₉ CH₃ 2163, 2219, 2275, 2331, n-C₄H₉ C₂H₅ 2164, 2220, 2276, 2332, n-C₄H₉ n-C₃H₇ 2165, 2221, 2277, 2333, n-C₄H₉ n-C₄H₉ 2166, 2222, 2278, 2334, n-C₄H₉ n-C₅H₁₁ 2167, 2223, 2279, 2335, n-C₄H₉ n-C₆H₁₃ 2168, 2224, 2280, 2336, n-C₄H₉ n-C₇H₁₅ 2169, 2225, 2281, 2337, n-C₅H₁₁ CH₃ 2170, 2226, 2282, 2338, n-C₅H₁₁ C₂H₅ 2171, 2227, 2283, 2339, n-C₅H₁₁ n-C₃H₇ 2172, 2228, 2284, 2340, n-C₅H₁₁ n-C₄H₉ 2173, 2229, 2285, 2341, n-C₅H₁₁ n-C₅H₁₁ 2174, 2230, 2286, 2342, n-C₅H₁₁ n-C₆H₁₃ 2175, 2231, 2287, 2343, n-C₅H₁₁ n-C₇H₁₅ 2176, 2232, 2288, 2344, n-C₆H₁₃ CH₃ 2177, 2233, 2289, 2345, n-C₆H₁₃ C₂H₅ 2178, 2234, 2290, 2346, n-C₆H₁₃ n-C₃H₇ 2179, 2235, 2291, 2347, n-C₆H₁₃ n-C₄H₉ 2180, 2236, 2292, 2348, n-C₆H₁₃ n-C₅H₁₁ 2181, 2237, 2293, 2349, n-C₆H₁₃ n-C₆H₁₃ 2182, 2238, 2294, 2350, n-C₆H₁₃ n-C₇H₁₅ 2183, 2239, 2295, 2351, n-C₇H₁₅ CH₃ 2184, 2240, 2296, 2352, n-C₇H₁₅ C₂H₅ 2185, 2241, 2297, 2353, n-C₇H₁₅ n-C₃H₇ 2186, 2242, 2298, 2354, n-C₇H₁₅ n-C₄H₉ 2187, 2243, 2299, 2355, n-C₇H₁₅ n-C₅H₁₁ 2188, 2244, 2300, 2356, n-C₇H₁₅ n-C₆H₁₃ 2189, 2245, 2301, 2357, n-C₇H₁₅ n-C₇H₁₅

Examples 2358-2621

Examples 2622-2885

Example No. X¹ X² R¹ R² 2358, 2622, H H H H 2359, 2623, H H H CH₃ 2360, 2624, H H H C₂H₅ 2361, 2625, H H H n-C₃H₇ 2362, 2626, H H H n-C₄H₉ 2363, 2627, H H H n-C₅H₁₁ 2364, 2628, H H H n-C₆H₁₃ 2365, 2629, H H H n-C₇H₁₅ 2366, 2630, F H H H 2367, 2631, F H H CH₃ 2368, 2632, F H H C₂H₅ 2369, 2633, F H H n-C₃H₇ 2370, 2634, F H H n-C₄H₉ 2371, 2635, F H H n-C₅H₁₁ 2372, 2636, F H H n-C₆H₁₃ 2373, 2637, F H H n-C₇H₁₅ 2374, 2638, F F H H 2375, 2639, F F H CH₃ 2376, 2640, F F H C₂H₅ 2377, 2641, F F H n-C₃H₇ 2378, 2642, F F H n-C₄H₉ 2379, 2643, F F H n-C₅H₁₁ 2380, 2644, F F H n-C₆H₁₃ 2381, 2645, F F H n-C₇H₁₅ 2382, 2646, CF₃ H H H 2383, 2647, CF₃ H H CH₃ 2384, 2648, CF₃ H H C₂H₅ 2385, 2649, CF₃ H H n-C₃H₇ 2386, 2650, CF₃ H H n-C₄H₉ 2387, 2651, CF₃ H H n-C₅H₁₁ 2388, 2652, CF₃ H H n-C₆H₁₃ 2389, 2653, CF₃ H H n-C₇H₁₅ 2390, 2654, —OCF₃ H H H 2391, 2655, —OCF₃ H H CH₃ 2392, 2656, —OCF₃ H H C₂H₅ 2393, 2657, —OCF₃ H H n-C₃H₇ 2394, 2658, —OCF₃ H H n-C₄H₉ 2395, 2659, —OCF₃ H H n-C₅H₁₁ 2396, 2660, —OCF₃ H H n-C₆H₁₃ 2397, 2661, —OCF₃ H H n-C₇H₁₅ 2398, 2662, H H CH₃ CH₃ 2399, 2663, H H CH₃ C₂H₅ 2400, 2664, H H CH₃ n-C₃H₇ 2401, 2665, H H CH₃ n-C₄H₉ 2402, 2666, H H CH₃ n-C₅H₁₁ 2403, 2667, H H CH₃ n-C₆H₁₃ 2404, 2668, H H CH₃ n-C₇H₁₅ 2405, 2669, F H CH₃ H 2406, 2670, F H CH₃ CH₃ 2407, 2671, F H CH₃ C₂H₅ 2408, 2672, F H CH₃ n-C₃H₇ 2409, 2673, F H CH₃ n-C₄H₉ 2410, 2674, F H CH₃ n-C₅H₁₁ 2411, 2675, F H CH₃ n-C₆H₁₃ 2412, 2676, F H CH₃ n-C₇H₁₅ 2413, 2677, F F CH₃ CH₃ 2414, 2678, F F CH₃ C₂H₅ 2415, 2679, F F CH₃ n-C₃H₇ 2416, 2680, F F CH₃ n-C₄H₉ 2417, 2681, F F CH₃ n-C₅H₁₁ 2418, 2682, F F CH₃ n-C₆H₁₃ 2419, 2683, F F CH₃ n-C₇H₁₅ 2420, 2684, CF₃ H CH₃ H 2421, 2685, CF₃ H CH₃ CH₃ 2422, 2686, CF₃ H CH₃ C₂H₅ 2423, 2687, CF₃ H CH₃ n-C₃H₇ 2424, 2688, CF₃ H CH₃ n-C₄H₉ 2425, 2689, CF₃ H CH₃ n-C₅H₁₁ 2426, 2690, CF₃ H CH₃ n-C₆H₁₃ 2427, 2691, CF₃ H CH₃ n-C₇H₁₅ 2428, 2692, —OCF₃ H CH₃ H 2429, 2693, —OCF₃ H CH₃ CH₃ 2430, 2694, —OCF₃ H CH₃ C₂H₅ 2431, 2695, —OCF₃ H CH₃ n-C₃H₇ 2432, 2696, —OCF₃ H CH₃ n-C₄H₉ 2433, 2697, —OCF₃ H CH₃ n-C₅H₁₁ 2434, 2698, —OCF₃ H CH₃ n-C₆H₁₃ 2435, 2699, —OCF₃ H CH₃ n-C₇H₁₅ 2436, 2700, H H C₂H₅ C₂H₅ 2437, 2701, H H C₂H₅ n-C₃H₇ 2438, 2702, H H C₂H₅ n-C₄H₉ 2439, 2703, H H C₂H₅ n-C₅H₁₁ 2440, 2704, H H C₂H₅ n-C₆H₁₃ 2441, 2705, H H C₂H₅ n-C₇H₁₅ 2442, 2706, F H C₂H₅ H 2443, 2707, F H C₂H₅ CH₃ 2444, 2708, F H C₂H₅ C₂H₅ 2445, 2709, F H C₂H₅ n-C₃H₇ 2446, 2710, F H C₂H₅ n-C₄H₉ 2447, 2711, F H C₂H₅ n-C₅H₁₁ 2448, 2712, F H C₂H₅ n-C₆H₁₃ 2449, 2713, F H C₂H₅ n-C₇H₁₅ 2450, 2714, F F C₂H₅ C₂H₅ 2451, 2715, F F C₂H₅ n-C₃H₇ 2452, 2716, F F C₂H₅ n-C₄H₉ 2453, 2717, F F C₂H₅ n-C₅H₁₁ 2454, 2718, F F C₂H₅ n-C₆H₁₃ 2455, 2719, F F C₂H₅ n-C₇H₁₅ 2456, 2720, CF₃ H C₂H₅ H 2457, 2721, CF₃ H C₂H₅ CH₃ 2458, 2722, CF₃ H C₂H₅ C₂H₅ 2459, 2723, CF₃ H C₂H₅ n-C₃H₇ 2460, 2724, CF₃ H C₂H₅ n-C₄H₉ 2461, 2725, CF₃ H C₂H₅ n-C₅H₁₁ 2462, 2726, CF₃ H C₂H₅ n-C₆H₁₃ 2463, 2727, CF₃ H C₂H₅ n-C₇H₁₅ 2464, 2728, —OCF₃ H C₂H₅ H 2465, 2729, —OCF₃ H C₂H₅ CH₃ 2466, 2730, —OCF₃ H C₂H₅ C₂H₅ 2467, 2731, —OCF₃ H C₂H₅ n-C₃H₇ 2468, 2732, —OCF₃ H C₂H₅ n-C₄H₉ 2469, 2733, —OCF₃ H C₂H₅ n-C₅H₁₁ 2470, 2734, —OCF₃ H C₂H₅ n-C₆H₁₃ 2471, 2735, —OCF₃ H C₂H₅ n-C₇H₁₅ 2472, 2736, H H n-C₃H₇ n-C₃H₇ 2473, 2737, H H n-C₃H₇ n-C₄H₉ 2474, 2738, H H n-C₃H₇ n-C₅H₁₁ 2475, 2739, H H n-C₃H₇ n-C₆H₁₃ 2476, 2740, H H n-C₃H₇ n-C₇H₁₅ 2477, 2741, F H n-C₃H₇ H 2478, 2742, F H n-C₃H₇ CH₃ 2479, 2743, F H n-C₃H₇ C₂H₅ 2480, 2744, F H n-C₃H₇ n-C₃H₇ 2481, 2745, F H n-C₃H₇ n-C₄H₉ 2482, 2746, F H n-C₃H₇ n-C₅H₁₁ 2483, 2747, F H n-C₃H₇ n-C₆H₁₃ 2484, 2748, F H n-C₃H₇ n-C₇H₁₅ 2485, 2749, F F n-C₃H₇ n-C₃H₇ 2486, 2750, F F n-C₃H₇ n-C₄H₉ 2487, 2751, F F n-C₃H₇ n-C₅H₁₁ 2488, 2752, F F n-C₃H₇ n-C₆H₁₃ 2489, 2753, F F n-C₃H₇ n-C₇H₁₅ 2490, 2754, CF₃ H n-C₃H₇ H 2491, 2755, CF₃ H n-C₃H₇ CH₃ 2492, 2756, CF₃ H n-C₃H₇ C₂H₅ 2493, 2757, CF₃ H n-C₃H₇ n-C₃H₇ 2494, 2758, CF₃ H n-C₃H₇ n-C₄H₉ 2495, 2759, CF₃ H n-C₃H₇ n-C₅H₁₁ 2496, 2760, CF₃ H n-C₃H₇ n-C₆H₁₃ 2497, 2761, CF₃ H n-C₃H₇ n-C₇H₁₅ 2498, 2762, —OCF₃ H n-C₃H₇ H 2499, 2763, —OCF₃ H n-C₃H₇ CH₃ 2500, 2764, —OCF₃ H n-C₃H₇ C₂H₅ 2501, 2765, —OCF₃ H n-C₃H₇ n-C₃H₇ 2502, 2766, —OCF₃ H n-C₃H₇ n-C₄H₉ 2503, 2767, —OCF₃ H n-C₃H₇ n-C₅H₁₁ 2504, 2768, —OCF₃ H n-C₃H₇ n-C₆H₁₃ 2505, 2769, —OCF₃ H n-C₃H₇ n-C₇H₁₅ 2506, 2770, H H n-C₄H₉ n-C₄H₉ 2507, 2771, H H n-C₄H₉ n-C₅H₁₁ 2508, 2772, H H n-C₄H₉ n-C₆H₁₃ 2509, 2773, H H n-C₄H₉ n-C₇H₁₅ 2510, 2774, F H n-C₄H₉ H 2511, 2775, F H n-C₄H₉ CH₃ 2512, 2776, F H n-C₄H₉ C₂H₅ 2513, 2777, F H n-C₄H₉ n-C₃H₇ 2514, 2778, F H n-C₄H₉ n-C₄H₉ 2515, 2779, F H n-C₄H₉ n-C₅H₁₁ 2516, 2780, F H n-C₄H₉ n-C₆H₁₃ 2517, 2781, F H n-C₄H₉ n-C₇H₁₅ 2518, 2782, F F n-C₄H₉ n-C₄H₉ 2519, 2783, F F n-C₄H₉ n-C₅H₁₁ 2520, 2784, F F n-C₄H₉ n-C₆H₁₃ 2521, 2785, F F n-C₄H₉ n-C₇H₁₅ 2522, 2786, CF₃ H n-C₄H₉ H 2523, 2787, CF₃ H n-C₄H₉ CH₃ 2524, 2788, CF₃ H n-C₄H₉ C₂H₅ 2525, 2789, CF₃ H n-C₄H₉ n-C₃H₇ 2526, 2790, CF₃ H n-C₄H₉ n-C₄H₉ 2527, 2791, CF₃ H n-C₄H₉ n-C₅H₁₁ 2528, 2792, CF₃ H n-C₄H₉ n-C₆H₁₃ 2529, 2793, CF₃ H n-C₄H₉ n-C₇H₁₅ 2530, 2794, —OCF₃ H n-C₄H₉ H 2531, 2795, —OCF₃ H n-C₄H₉ CH₃ 2532, 2796, —OCF₃ H n-C₄H₉ C₂H₅ 2533, 2797, —OCF₃ H n-C₄H₉ n-C₃H₇ 2534, 2798, —OCF₃ H n-C₄H₉ n-C₄H₉ 2535, 2799, —OCF₃ H n-C₄H₉ n-C₅H₁₁ 2536, 2800, —OCF₃ H n-C₄H₉ n-C₆H₁₃ 2537, 2801, —OCF₃ H n-C₄H₉ n-C₇H₁₅ 2538, 2802, H H n-C₅H₁₁ n-C₅H₁₁ 2539, 2803, H H n-C₅H₁₁ n-C₆H₁₃ 2540, 2804, H H n-C₅H₁₁ n-C₇H₁₅ 2541, 2805, F H n-C₅H₁₁ H 2542, 2806, F H n-C₅H₁₁ CH₃ 2543, 2807, F H n-C₅H₁₁ C₂H₅ 2544, 2808, F H n-C₅H₁₁ n-C₃H₇ 2545, 2809, F H n-C₅H₁₁ n-C₄H₉ 2546, 2810, F H n-C₅H₁₁ n-C₅H₁₁ 2547, 2811, F H n-C₅H₁₁ n-C₆H₁₃ 2548, 2812, F H n-C₅H₁₁ n-C₇H₁₅ 2549, 2813, F F n-C₅H₁₁ n-C₅H₁₁ 2550, 2814, F F n-C₅H₁₁ n-C₆H₁₃ 2551, 2815, F F n-C₅H₁₁ n-C₇H₁₅ 2552, 2816, CF₃ H n-C₅H₁₁ H 2553, 2817, CF₃ H n-C₅H₁₁ CH₃ 2554, 2818, CF₃ H n-C₅H₁₁ C₂H₅ 2555, 2819, CF₃ H n-C₅H₁₁ n-C₃H₇ 2556, 2820, CF₃ H n-C₅H₁₁ n-C₄H₉ 2557, 2821, CF₃ H n-C₅H₁₁ n-C₅H₁₁ 2558, 2822, CF₃ H n-C₅H₁₁ n-C₆H₁₃ 2559, 2823, CF₃ H n-C₅H₁₁ n-C₇H₁₅ 2560, 2824, —OCF₃ H n-C₅H₁₁ H 2561, 2825, —OCF₃ H n-C₅H₁₁ CH₃ 2562, 2826, —OCF₃ H n-C₅H₁₁ C₂H₅ 2563, 2827, —OCF₃ H n-C₅H₁₁ n-C₃H₇ 2564, 2828, —OCF₃ H n-C₅H₁₁ n-C₄H₉ 2565, 2829, —OCF₃ H n-C₅H₁₁ n-C₅H₁₁ 2566, 2830, —OCF₃ H n-C₅H₁₁ n-C₆H₁₃ 2567, 2831, —OCF₃ H n-C₅H₁₁ n-C₇H₁₅ 2568, 2832, H H n-C₆H₁₃ n-C₆H₁₃ 2569, 2833, H H n-C₆H₁₃ n-C₇H₁₅ 2570, 2834, F H n-C₆H₁₃ H 2571, 2835, F H n-C₆H₁₃ CH₃ 2572, 2836, F H n-C₆H₁₃ C₂H₅ 2573, 2837, F H n-C₆H₁₃ n-C₃H₇ 2574, 2838, F H n-C₆H₁₃ n-C₄H₉ 2575, 2839, F H n-C₆H₁₃ n-C₅H₁₁ 2576, 2840, F H n-C₆H₁₃ n-C₆H₁₃ 2577, 2841, F H n-C₆H₁₃ n-C₇H₁₅ 2578, 2842, F F n-C₆H₁₃ n-C₆H₁₃ 2579, 2843, F F n-C₆H₁₃ n-C₇H₁₅ 2580, 2844, CF₃ H n-C₆H₁₃ H 2581, 2845, CF₃ H n-C₆H₁₃ CH₃ 2582, 2846, CF₃ H n-C₆H₁₃ C₂H₅ 2583, 2847, CF₃ H n-C₆H₁₃ n-C₃H₇ 2584, 2848, CF₃ H n-C₆H₁₃ n-C₄H₉ 2585, 2849, CF₃ H n-C₆H₁₃ n-C₅H₁₁ 2586, 2850, CF₃ H n-C₆H₁₃ n-C₆H₁₃ 2587, 2851, CF₃ H n-C₆H₁₃ n-C₇H₁₅ 2588, 2852, —OCF₃ H n-C₆H₁₃ H 2589, 2853, —OCF₃ H n-C₆H₁₃ CH₃ 2590, 2854, —OCF₃ H n-C₆H₁₃ C₂H₅ 2591, 2855, —OCF₃ H n-C₆H₁₃ n-C₃H₇ 2592, 2856, —OCF₃ H n-C₆H₁₃ n-C₄H₉ 2593, 2857, —OCF₃ H n-C₆H₁₃ n-C₅H₁₁ 2594, 2858, —OCF₃ H n-C₆H₁₃ n-C₆H₁₃ 2595, 2859, —OCF₃ H n-C₆H₁₃ n-C₇H₁₅ 2596, 2860, H H n-C₇H₁₅ n-C₇H₁₅ 2597, 2861, F H n-C₇H₁₅ H 2598, 2862, F H n-C₇H₁₅ CH₃ 2599, 2863, F H n-C₇H₁₅ C₂H₅ 2600, 2864, F H n-C₇H₁₅ n-C₃H₇ 2601, 2865, F H n-C₇H₁₅ n-C₄H₉ 2602, 2866, F H n-C₇H₁₅ n-C₅H₁₁ 2603, 2867, F H n-C₇H₁₅ n-C₆H₁₃ 2604, 2868, F H n-C₇H₁₅ n-C₇H₁₅ 2605, 2869, F F n-C₇H₁₅ n-C₇H₁₅ 2606, 2870, CF₃ H n-C₇H₁₅ H 2607, 2871, CF₃ H n-C₇H₁₅ CH₃ 2608, 2872, CF₃ H n-C₇H₁₅ C₂H₅ 2609, 2873, CF₃ H n-C₇H₁₅ n-C₃H₇ 2610, 2874, CF₃ H n-C₇H₁₅ n-C₄H₉ 2611, 2875, CF₃ H n-C₇H₁₅ n-C₅H₁₁ 2612, 2876, CF₃ H n-C₇H₁₅ n-C₆H₁₃ 2613, 2877, CF₃ H n-C₇H₁₅ n-C₇H₁₅ 2614, 2878, —OCF₃ H n-C₇H₁₅ H 2615, 2879, —OCF₃ H n-C₇H₁₅ CH₃ 2616, 2880, —OCF₃ H n-C₇H₁₅ C₂H₅ 2617, 2881, —OCF₃ H n-C₇H₁₅ n-C₃H₇ 2618, 2882, —OCF₃ H n-C₇H₁₅ n-C₄H₉ 2619, 2883, —OCF₃ H n-C₇H₁₅ n-C₅H₁₁ 2620, 2884, —OCF₃ H n-C₇H₁₅ n-C₆H₁₃ 2621, 2885, —OCF₃ H n-C₇H₁₅ n-C₇H₁₅

Examples 2886-2949

Examples 2950-3013

Examples 3014-3077

Examples 3078-3141

Example No. R¹ R² 2886, 2950, 3014, 3078, H H 2887, 2951, 3015, 3079, H CH₃ 2888, 2952, 3016, 3080, H C₂H₅ 2889, 2953, 3017, 3081, H n-C₃H₇ 2890, 2954, 3018, 3082, H n-C₄H₉ 2891, 2955, 3019, 3083, H n-C₅H₁₁ 2892, 2956, 3020, 3084, H n-C₆H₁₃ 2893, 2957, 3021, 3085, H n-C₇H₁₅ 2894, 2958, 3022, 3086, CH₃ H 2895, 2959, 3023, 3087, CH₃ CH₃ 2896, 2960, 3024, 3088, CH₃ C₂H₅ 2897, 2961, 3025, 3089, CH₃ n-C₃H₇ 2898, 2962, 3026, 3090, CH₃ n-C₄H₉ 2899, 2963, 3027, 3091, CH₃ n-C₅H₁₁ 2900, 2964, 3028, 3092, CH₃ n-C₆H₁₃ 2901, 2965, 3029, 3093, CH₃ n-C₇H₁₅ 2902, 2966, 3030, 3094, C₂H₅ H 2903, 2967, 3031, 3095, C₂H₅ CH₃ 2904, 2968, 3032, 3096, C₂H₅ C₂H₅ 2905, 2969, 3033, 3097, C₂H₅ n-C₃H₇ 2906, 2970, 3034, 3098, C₂H₅ n-C₄H₉ 2907, 2971, 3035, 3099, C₂H₅ n-C₅H₁₁ 2908, 2972, 3036, 3100, C₂H₅ n-C₆H₁₃ 2909, 2973, 3037, 3101, C₂H₅ n-C₇H₁₅ 2910, 2974, 3038, 3102, n-C₃H₇ H 2911, 2975, 3039, 3103, n-C₃H₇ CH₃ 2912, 2976, 3040, 3104, n-C₃H₇ C₂H₅ 2913, 2977, 3041, 3105, n-C₃H₇ n-C₃H₇ 2914, 2978, 3042, 3106, n-C₃H₇ n-C₄H₉ 2915, 2979, 3043, 3107, n-C₃H₇ n-C₅H₁₁ 2916, 2980, 3044, 3108, n-C₃H₇ n-C₆H₁₃ 2917, 2981, 3045, 3109, n-C₃H₇ n-C₇H₁₅ 2918, 2982, 3046, 3110, n-C₄H₉ H 2919, 2983, 3047, 3111, n-C₄H₉ CH₃ 2920, 2984, 3048, 3112, n-C₄H₉ C₂H₅ 2921, 2985, 3049, 3113, n-C₄H₉ n-C₃H₇ 2922, 2986, 3050, 3114, n-C₄H₉ n-C₄H₉ 2923, 2987, 3051, 3115, n-C₄H₉ n-C₅H₁₁ 2924, 2988, 3052, 3116, n-C₄H₉ n-C₆H₁₃ 2925, 2989, 3053, 3117, n-C₄H₉ n-C₇H₁₅ 2926, 2990, 3054, 3118, n-C₅H₁₁ H 2927, 2991, 3055, 3119, n-C₅H₁₁ CH₃ 2928, 2992, 3056, 3120, n-C₅H₁₁ C₂H₅ 2929, 2993, 3057, 3121, n-C₅H₁₁ n-C₃H₇ 2930, 2994, 3058, 3122, n-C₅H₁₁ n-C₄H₉ 2931, 2995, 3059, 3123, n-C₅H₁₁ n-C₅H₁₁ 2932, 2996, 3060, 3124, n-C₅H₁₁ n-C₆H₁₃ 2933, 2997, 3061, 3125, n-C₅H₁₁ n-C₇H₁₅ 2934, 2998, 3062, 3126, n-C₆H₁₃ H 2935, 2999, 3063, 3127, n-C₆H₁₃ CH₃ 2936, 3000, 3064, 3128, n-C₆H₁₃ C₂H₅ 2937, 3001, 3065, 3129, n-C₆H₁₃ n-C₃H₇ 2938, 3002, 3066, 3130, n-C₆H₁₃ n-C₄H₉ 2939, 3003, 3067, 3131, n-C₆H₁₃ n-C₅H₁₁ 2940, 3004, 3068, 3132, n-C₆H₁₃ n-C₆H₁₃ 2941, 3005, 3069, 3133, n-C₆H₁₃ n-C₇H₁₅ 2942, 3006, 3070, 3134, n-C₇H₁₅ H 2943, 3007, 3071, 3135, n-C₇H₁₅ CH₃ 2944, 3008, 3072, 3136, n-C₇H₁₅ C₂H₅ 2945, 3009, 3073, 3137, n-C₇H₁₅ n-C₃H₇ 2946, 3010, 3074, 3138, n-C₇H₁₅ n-C₄H₉ 2947, 3011, 3075, 3139, n-C₇H₁₅ n-C₅H₁₁ 2948, 3012, 3076, 3140, n-C₇H₁₅ n-C₆H₁₃ 2949, 3013, 3077, 3141, n-C₇H₁₅ n-C₇H₁₅

Examples 3142-3205

Examples 3206-3269

Examples 3270-3333

Examples 3334-3397

Example No. R¹ R² 3142, 3206, 3270, 3334, H H 3143, 3207, 3271, 3335, H CH₃ 3144, 3208, 3272, 3336, H C₂H₅ 3145, 3209, 3273, 3337, H n-C₃H₇ 3146, 3210, 3274, 3338, H n-C₄H₉ 3147, 3211, 3275, 3339, H n-C₅H₁₁ 3148, 3212, 3276, 3340, H n-C₆H₁₃ 3149, 3213, 3277, 3341, H n-C₇H₁₅ 3150, 3214, 3278, 3342, CH₃ H 3151, 3215, 3279, 3343, CH₃ CH₃ 3152, 3216, 3280, 3344, CH₃ C₂H₅ 3153, 3217, 3281, 3345, CH₃ n-C₃H₇ 3154, 3218, 3282, 3346, CH₃ n-C₄H₉ 3155, 3219, 3283, 3347, CH₃ n-C₅H₁₁ 3156, 3220, 3284, 3348, CH₃ n-C₆H₁₃ 3157, 3221, 3285, 3349, CH₃ n-C₇H₁₅ 3158, 3222, 3286, 3350, C₂H₅ H 3159, 3223, 3287, 3351, C₂H₅ CH₃ 3160, 3224, 3288, 3352, C₂H₅ C₂H₅ 3161, 3225, 3289, 3353, C₂H₅ n-C₃H₇ 3162, 3226, 3290, 3354, C₂H₅ n-C₄H₉ 3163, 3227, 3291, 3355, C₂H₅ n-C₅H₁₁ 3164, 3228, 3292, 3356, C₂H₅ n-C₆H₁₃ 3165, 3229, 3293, 3357, C₂H₅ n-C₇H₁₅ 3166, 3230, 3294, 3358, n-C₃H₇ H 3167, 3231, 3295, 3359, n-C₃H₇ CH₃ 3168, 3232, 3296, 3360, n-C₃H₇ C₂H₅ 3169, 3233, 3297, 3361, n-C₃H₇ n-C₃H₇ 3170, 3234, 3298, 3362, n-C₃H₇ n-C₄H₉ 3171, 3235, 3299, 3363, n-C₃H₇ n-C₅H₁₁ 3172, 3236, 3300, 3364, n-C₃H₇ n-C₆H₁₃ 3173, 3237, 3301, 3365, n-C₃H₇ n-C₇H₁₅ 3174, 3238, 3302, 3366, n-C₄H₉ H 3175, 3239, 3303, 3367, n-C₄H₉ CH₃ 3176, 3240, 3304, 3368, n-C₄H₉ C₂H₅ 3177, 3241, 3305, 3369, n-C₄H₉ n-C₃H₇ 3178, 3242, 3306, 3370, n-C₄H₉ n-C₄H₉ 3179, 3243, 3307, 3371, n-C₄H₉ n-C₅H₁₁ 3180, 3244, 3308, 3372, n-C₄H₉ n-C₆H₁₃ 3181, 3245, 3309, 3373, n-C₄H₉ n-C₇H₁₅ 3182, 3246, 3310, 3374, n-C₅H₁₁ H 3183, 3247, 3311, 3375, n-C₅H₁₁ CH₃ 3184, 3248, 3312, 3376, n-C₅H₁₁ C₂H₅ 3185, 3249, 3313, 3377, n-C₅H₁₁ n-C₃H₇ 3186, 3250, 3314, 3378, n-C₅H₁₁ n-C₄H₉ 3187, 3251, 3315, 3379, n-C₅H₁₁ n-C₅H₁₁ 3188, 3252, 3316, 3380, n-C₅H₁₁ n-C₆H₁₃ 3189, 3253, 3317, 3381, n-C₅H₁₁ n-C₇H₁₅ 3190, 3254, 3318, 3382, n-C₆H₁₃ H 3191, 3255, 3319, 3383, n-C₆H₁₃ CH₃ 3192, 3256, 3320, 3384, n-C₆H₁₃ C₂H₅ 3193, 3257, 3321, 3385, n-C₆H₁₃ n-C₃H₇ 3194, 3258, 3322, 3386, n-C₆H₁₃ n-C₄H₉ 3195, 3259, 3323, 3387, n-C₆H₁₃ n-C₅H₁₁ 3196, 3260, 3324, 3388, n-C₆H₁₃ n-C₆H₁₃ 3197, 3261, 3325, 3389, n-C₆H₁₃ n-C₇H₁₅ 3198, 3262, 3326, 3390, n-C₇H₁₅ H 3199, 3263, 3327, 3391, n-C₇H₁₅ CH₃ 3200, 3264, 3328, 3392, n-C₇H₁₅ C₂H₅ 3201, 3265, 3329, 3393, n-C₇H₁₅ n-C₃H₇ 3202, 3266, 3330, 3394, n-C₇H₁₅ n-C₄H₉ 3203, 3267, 3331, 3395, n-C₇H₁₅ n-C₅H₁₁ 3204, 3268, 3332, 3396, n-C₇H₁₅ n-C₆H₁₃ 3205, 3269, 3333, 3397, n-C₇H₁₅ n-C₇H₁₅

Examples 3398-3461

Examples 3462-3525

Examples 3526-3589

Examples 3590-3653

Example No. R¹ R² 3398, 3462, 3526, 3590, H H 3399, 3463, 3527, 3591, H CH₃ 3400, 3464, 3528, 3592, H C₂H₅ 3401, 3465, 3529, 3593, H n-C₃H₇ 3402, 3466, 3530, 3594, H n-C₄H₉ 3403, 3467, 3531, 3595, H n-C₅H₁₁ 3404, 3468, 3532, 3596, H n-C₆H₁₃ 3405, 3469, 3533, 3597, H n-C₇H₁₅ 3406, 3470, 3534, 3598, CH₃ H 3407, 3471, 3535, 3599, CH₃ CH₃ 3408, 3472, 3536, 3600, CH₃ C₂H₅ 3409, 3473, 3537, 3601, CH₃ n-C₃H₇ 3410, 3474, 3538, 3602, CH₃ n-C₄H₉ 3411, 3475, 3539, 3603, CH₃ n-C₅H₁₁ 3412, 3476, 3540, 3604, CH₃ n-C₆H₁₃ 3413, 3477, 3541, 3605, CH₃ n-C₇H₁₅ 3414, 3478, 3542, 3606, C₂H₅ H 3415, 3479, 3543, 3607, C₂H₅ CH₃ 3416, 3480, 3544, 3608, C₂H₅ C₂H₅ 3417, 3481, 3545, 3609, C₂H₅ n-C₃H₇ 3418, 3482, 3546, 3610, C₂H₅ n-C₄H₉ 3419, 3483, 3547, 3611, C₂H₅ n-C₅H₁₁ 3420, 3484, 3548, 3612, C₂H₅ n-C₆H₁₃ 3421, 3485, 3549, 3613, C₂H₅ n-C₇H₁₅ 3422, 3486, 3550, 3614, n-C₃H₇ H 3423, 3487, 3551, 3615, n-C₃H₇ CH₃ 3424, 3488, 3552, 3616, n-C₃H₇ C₂H₅ 3425, 3489, 3553, 3617, n-C₃H₇ n-C₃H₇ 3426, 3490, 3554, 3618, n-C₃H₇ n-C₄H₉ 3427, 3491, 3555, 3619, n-C₃H₇ n-C₅H₁₁ 3428, 3492, 3556, 3620, n-C₃H₇ n-C₆H₁₃ 3429, 3493, 3557, 3621, n-C₃H₇ n-C₇H₁₅ 3430, 3494, 3558, 3622, n-C₄H₉ H 3431, 3495, 3559, 3623, n-C₄H₉ CH₃ 3432, 3496, 3560, 3624, n-C₄H₉ C₂H₅ 3433, 3497, 3561, 3625, n-C₄H₉ n-C₃H₇ 3434, 3498, 3562, 3626, n-C₄H₉ n-C₄H₉ 3435, 3499, 3563, 3627, n-C₄H₉ n-C₅H₁₁ 3436, 3500, 3564, 3628, n-C₄H₉ n-C₆H₁₃ 3437, 3501, 3565, 3629, n-C₄H₉ n-C₇H₁₅ 3438, 3502, 3566, 3630, n-C₅H₁₁ H 3439, 3503, 3567, 3631, n-C₅H₁₁ CH₃ 3440, 3504, 3568, 3632, n-C₅H₁₁ C₂H₅ 3441, 3505, 3569, 3633, n-C₅H₁₁ n-C₃H₇ 3442, 3506, 3570, 3634, n-C₅H₁₁ n-C₄H₉ 3443, 3507, 3571, 3635, n-C₅H₁₁ n-C₅H₁₁ 3444, 3508, 3572, 3636, n-C₅H₁₁ n-C₆H₁₃ 3445, 3509, 3573, 3637, n-C₅H₁₁ n-C₇H₁₅ 3446, 3510, 3574, 3638, n-C₆H₁₃ H 3447, 3511, 3575, 3639, n-C₆H₁₃ CH₃ 3448, 3512, 3576, 3640, n-C₆H₁₃ C₂H₅ 3449, 3513, 3577, 3641, n-C₆H₁₃ n-C₃H₇ 3450, 3514, 3578, 3642, n-C₆H₁₃ n-C₄H₉ 3451, 3515, 3579, 3643, n-C₆H₁₃ n-C₅H₁₁ 3452, 3516, 3580, 3644, n-C₆H₁₃ n-C₆H₁₃ 3453, 3517, 3581, 3645, n-C₆H₁₃ n-C₇H₁₅ 3454, 3518, 3582, 3646, n-C₇H₁₅ H 3455, 3519, 3583, 3647, n-C₇H₁₅ CH₃ 3456, 3520, 3584, 3648, n-C₇H₁₅ C₂H₅ 3457, 3521, 3585, 3649, n-C₇H₁₅ n-C₃H₇ 3458, 3522, 3586, 3650, n-C₇H₁₅ n-C₄H₉ 3459, 3523, 3587, 3651, n-C₇H₁₅ n-C₅H₁₁ 3460, 3524, 3588, 3652, n-C₇H₁₅ n-C₆H₁₃ 3461, 3525, 3589, 3653, n-C₇H₁₅ n-C₇H₁₅

Examples 3654-3912

Example No. X¹ X² R¹ R² 3654, H H H CH₃ 3655, H H H C₂H₅ 3656, H H H n-C₃H₇ 3657, H H H n-C₄H₉ 3658, H H H n-C₅H₁₁ 3659, H H H n-C₆H₁₃ 3660, H H H n-C₇H₁₅ 3661, F H H CH₃ 3662, F H H C₂H₅ 3663, F H H n-C₃H₇ 3664, F H H n-C₄H₉ 3665, F H H n-C₅H₁₁ 3666, F H H n-C₆H₁₃ 3667, F H H n-C₇H₁₅ 3668, H F H CH₃ 3669, H F H C₂H₅ 3670, H F H n-C₃H₇ 3671, H F H n-C₄H₉ 3672, H F H n-C₅H₁₁ 3673, H F H n-C₆H₁₃ 3674, H F H n-C₇H₁₅ 3675, F F H CH₃ 3676, F F H C₂H₅ 3677, F F H n-C₃H₇ 3678, F F H n-C₄H₉ 3679, F F H n-C₅H₁₁ 3680, F F H n-C₆H₁₃ 3681, F F H n-C₇H₁₅ 3682, CF₃ H H CH₃ 3683, CF₃ H H C₂H₅ 3684, CF₃ H H n-C₃H₇ 3685, CF₃ H H n-C₄H₉ 3686, CF₃ H H n-C₅H₁₁ 3687, CF₃ H H n-C₆H₁₃ 3688, CF₃ H H n-C₇H₁₅ 3689, H CF₃ H CH₃ 3690, H CF₃ H C₂H₅ 3691, H CF₃ H n-C₃H₇ 3692, H CF₃ H n-C₄H₉ 3693, H CF₃ H n-C₅H₁₁ 3694, H CF₃ H n-C₆H₁₃ 3695, H CF₃ H n-C₇H₁₅ 3696, —OCF₃ H H CH₃ 3697, —OCF₃ H H C₂H₅ 3698, —OCF₃ H H n-C₃H₇ 3699, —OCF₃ H H n-C₄H₉ 3700, —OCF₃ H H n-C₅H₁₁ 3701, —OCF₃ H H n-C₆H₁₃ 3702, —OCF₃ H H n-C₇H₁₅ 3703, H —OCF₃ H CH₃ 3704, H —OCF₃ H C₂H₅ 3705, H —OCF₃ H n-C₃H₇ 3706, H —OCF₃ H n-C₄H₉ 3707, H —OCF₃ H n-C₅H₁₁ 3708, H —OCF₃ H n-C₆H₁₃ 3709, H —OCF₃ H n-C₇H₁₅ 3710, H H CH₃ CH₃ 3711, H H CH₃ C₂H₅ 3712, H H CH₃ n-C₃H₇ 3713, H H CH₃ n-C₄H₉ 3714, H H CH₃ n-C₅H₁₁ 3715, H H CH₃ n-C₆H₁₃ 3716, H H CH₃ n-C₇H₁₅ 3717, F H CH₃ CH₃ 3718, F H CH₃ C₂H₅ 3719, F H CH₃ n-C₃H₇ 3720, F H CH₃ n-C₄H₉ 3721, F H CH₃ n-C₅H₁₁ 3722, F H CH₃ n-C₆H₁₃ 3723, F H CH₃ n-C₇H₁₅ 3724, F F CH₃ CH₃ 3725, F F CH₃ C₂H₅ 3726, F F CH₃ n-C₃H₇ 3727, F F CH₃ n-C₄H₉ 3728, F F CH₃ n-C₅H₁₁ 3729, F F CH₃ n-C₆H₁₃ 3730, F F CH₃ n-C₇H₁₅ 3731, CF₃ H CH₃ CH₃ 3732, CF₃ H CH₃ C₂H₅ 3733, CF₃ H CH₃ n-C₃H₇ 3734, CF₃ H CH₃ n-C₄H₉ 3735, CF₃ H CH₃ n-C₅H₁₁ 3736, CF₃ H CH₃ n-C₆H₁₃ 3737, CF₃ H CH₃ n-C₇H₁₅ 3738, —OCF₃ H CH₃ CH₃ 3739, —OCF₃ H CH₃ C₂H₅ 3740, —OCF₃ H CH₃ n-C₃H₇ 3741, —OCF₃ H CH₃ n-C₄H₉ 3742, —OCF₃ H CH₃ n-C₅H₁₁ 3743, —OCF₃ H CH₃ n-C₆H₁₃ 3744, —OCF₃ H CH₃ n-C₇H₁₅ 3745, H H C₂H₅ C₂H₅ 3746, H H C₂H₅ n-C₃H₇ 3747, H H C₂H₅ n-C₄H₉ 3748, H H C₂H₅ n-C₅H₁₁ 3749, H H C₂H₅ n-C₆H₁₃ 3750, H H C₂H₅ n-C₇H₁₅ 3751, F H C₂H₅ CH₃ 3752, F H C₂H₅ C₂H₅ 3753, F H C₂H₅ n-C₃H₇ 3754, F H C₂H₅ n-C₄H₉ 3755, F H C₂H₅ n-C₅H₁₁ 3756, F H C₂H₅ n-C₆H₁₃ 3757, F H C₂H₅ n-C₇H₁₅ 3758, F F C₂H₅ C₂H₅ 3759, F F C₂H₅ n-C₃H₇ 3760, F F C₂H₅ n-C₄H₉ 3761, F F C₂H₅ n-C₅H₁₁ 3762, F F C₂H₅ n-C₆H₁₃ 3763, F F C₂H₅ n-C₇H₁₅ 3764, CF₃ H C₂H₅ CH₃ 3765, CF₃ H C₂H₅ C₂H₅ 3766, CF₃ H C₂H₅ n-C₃H₇ 3767, CF₃ H C₂H₅ n-C₄H₉ 3768, CF₃ H C₂H₅ n-C₅H₁₁ 3769, CF₃ H C₂H₅ n-C₆H₁₃ 3770, CF₃ H C₂H₅ n-C₇H₁₅ 3771, —OCF₃ H C₂H₅ CH₃ 3772, —OCF₃ H C₂H₅ C₂H₅ 3773, —OCF₃ H C₂H₅ n-C₃H₇ 3774, —OCF₃ H C₂H₅ n-C₄H₉ 3775, —OCF₃ H C₂H₅ n-C₅H₁₁ 3776, —OCF₃ H C₂H₅ n-C₆H₁₃ 3777, —OCF₃ H C₂H₅ n-C₇H₁₅ 3778, H H n-C₃H₇ n-C₃H₇ 3779, H H n-C₃H₇ n-C₄H₉ 3780, H H n-C₃H₇ n-C₅H₁₁ 3781, H H n-C₃H₇ n-C₆H₁₃ 3782, H H n-C₃H₇ n-C₇H₁₅ 3783, F H n-C₃H₇ CH₃ 3784, F H n-C₃H₇ C₂H₅ 3785, F H n-C₃H₇ n-C₃H₇ 3786, F H n-C₃H₇ n-C₄H₉ 3787, F H n-C₃H₇ n-C₅H₁₁ 3788, F H n-C₃H₇ n-C₆H₁₃ 3789, F H n-C₃H₇ n-C₇H₁₅ 3790, F F n-C₃H₇ n-C₃H₇ 3791, F F n-C₃H₇ n-C₄H₉ 3792, F F n-C₃H₇ n-C₅H₁₁ 3793, F F n-C₃H₇ n-C₆H₁₃ 3794, F F n-C₃H₇ n-C₇H₁₅ 3795, CF₃ H n-C₃H₇ CH₃ 3796, CF₃ H n-C₃H₇ C₂H₅ 3797, CF₃ H n-C₃H₇ n-C₃H₇ 3798, CF₃ H n-C₃H₇ n-C₄H₉ 3799, CF₃ H n-C₃H₇ n-C₅H₁₁ 3800, CF₃ H n-C₃H₇ n-C₆H₁₃ 3801, CF₃ H n-C₃H₇ n-C₇H₁₅ 3802, —OCF₃ H n-C₃H₇ CH₃ 3803, —OCF₃ H n-C₃H₇ C₂H₅ 3804, —OCF₃ H n-C₃H₇ n-C₃H₇ 3805, —OCF₃ H n-C₃H₇ n-C₄H₉ 3806, —OCF₃ H n-C₃H₇ n-C₅H₁₁ 3807, —OCF₃ H n-C₃H₇ n-C₆H₁₃ 3808, —OCF₃ H n-C₃H₇ n-C₇H₁₅ 3809, H H n-C₄H₉ n-C₄H₉ 3810, H H n-C₄H₉ n-C₅H₁₁ 3811, H H n-C₄H₉ n-C₆H₁₃ 3812, H H n-C₄H₉ n-C₇H₁₅ 3813, F H n-C₄H₉ CH₃ 3814, F H n-C₄H₉ C₂H₅ 3815, F H n-C₄H₉ n-C₃H₇ 3816, F H n-C₄H₉ n-C₄H₉ 3817, F H n-C₄H₉ n-C₅H₁₁ 3818, F H n-C₄H₉ n-C₆H₁₃ 3819, F H n-C₄H₉ n-C₇H₁₅ 3820, F F n-C₄H₉ n-C₄H₉ 3821, F F n-C₄H₉ n-C₅H₁₁ 3822, F F n-C₄H₉ n-C₆H₁₃ 3823, F F n-C₄H₉ n-C₇H₁₅ 3824, CF₃ H n-C₄H₉ CH₃ 3825, CF₃ H n-C₄H₉ C₂H₅ 3826, CF₃ H n-C₄H₉ n-C₃H₇ 3827, CF₃ H n-C₄H₉ n-C₄H₉ 3828, CF₃ H n-C₄H₉ n-C₅H₁₁ 3829, CF₃ H n-C₄H₉ n-C₆H₁₃ 3830, CF₃ H n-C₄H₉ n-C₇H₁₅ 3831, —OCF₃ H n-C₄H₉ CH₃ 3832, —OCF₃ H n-C₄H₉ C₂H₅ 3833, —OCF₃ H n-C₄H₉ n-C₃H₇ 3834, —OCF₃ H n-C₄H₉ n-C₄H₉ 3835, —OCF₃ H n-C₄H₉ n-C₅H₁₁ 3836, —OCF₃ H n-C₄H₉ n-C₆H₁₃ 3837, —OCF₃ H n-C₄H₉ n-C₇H₁₅ 3838, H H n-C₅H₁₁ n-C₅H₁₁ 3839, H H n-C₅H₁₁ n-C₆H₁₃ 3840, H H n-C₅H₁₁ n-C₇H₁₅ 3841, F H n-C₅H₁₁ CH₃ 3842, F H n-C₅H₁₁ C₂H₅ 3843, F H n-C₅H₁₁ n-C₃H₇ 3844, F H n-C₅H₁₁ n-C₄H₉ 3845, F H n-C₅H₁₁ n-C₅H₁₁ 3846, F H n-C₅H₁₁ n-C₆H₁₃ 3847, F H n-C₅H₁₁ n-C₇H₁₅ 3848, F F n-C₅H₁₁ n-C₅H₁₁ 3849, F F n-C₅H₁₁ n-C₆H₁₃ 3850, F F n-C₅H₁₁ n-C₇H₁₅ 3851, CF₃ H n-C₅H₁₁ CH₃ 3852, CF₃ H n-C₅H₁₁ C₂H₅ 3853, CF₃ H n-C₅H₁₁ n-C₃H₇ 3854, CF₃ H n-C₅H₁₁ n-C₄H₉ 3855, CF₃ H n-C₅H₁₁ n-C₅H₁₁ 3856, CF₃ H n-C₅H₁₁ n-C₆H₁₃ 3857, CF₃ H n-C₅H₁₁ n-C₇H₁₅ 3858, —OCF₃ H n-C₅H₁₁ CH₃ 3859, —OCF₃ H n-C₅H₁₁ C₂H₅ 3860, —OCF₃ H n-C₅H₁₁ n-C₃H₇ 3861, —OCF₃ H n-C₅H₁₁ n-C₄H₉ 3862, —OCF₃ H n-C₅H₁₁ n-C₅H₁₁ 3863, —OCF₃ H n-C₅H₁₁ n-C₆H₁₃ 3864, —OCF₃ H n-C₅H₁₁ n-C₇H₁₅ 3865, H H n-C₆H₁₃ n-C₆H₁₃ 3866, H H n-C₆H₁₃ n-C₇H₁₅ 3867, F H n-C₆H₁₃ CH₃ 3868, F H n-C₆H₁₃ C₂H₅ 3869, F H n-C₆H₁₃ n-C₃H₇ 3870, F H n-C₆H₁₃ n-C₄H₉ 3871, F H n-C₆H₁₃ n-C₅H₁₁ 3872, F H n-C₆H₁₃ n-C₆H₁₃ 3873, F H n-C₆H₁₃ n-C₇H₁₅ 3874, F F n-C₆H₁₃ n-C₆H₁₃ 3875, F F n-C₆H₁₃ n-C₇H₁₅ 3876, CF₃ H n-C₆H₁₃ CH₃ 3877, CF₃ H n-C₆H₁₃ C₂H₅ 3878, CF₃ H n-C₆H₁₃ n-C₃H₇ 3879, CF₃ H n-C₆H₁₃ n-C₄H₉ 3880, CF₃ H n-C₆H₁₃ n-C₅H₁₁ 3881, CF₃ H n-C₆H₁₃ n-C₆H₁₃ 3882, CF₃ H n-C₆H₁₃ n-C₇H₁₅ 3883, —OCF₃ H n-C₆H₁₃ CH₃ 3884, —OCF₃ H n-C₆H₁₃ C₂H₅ 3885, —OCF₃ H n-C₆H₁₃ n-C₃H₇ 3886, —OCF₃ H n-C₆H₁₃ n-C₄H₉ 3887, —OCF₃ H n-C₆H₁₃ n-C₅H₁₁ 3888, —OCF₃ H n-C₆H₁₃ n-C₆H₁₃ 3889, —OCF₃ H n-C₆H₁₃ n-C₇H₁₅ 3890, H H n-C₇H₁₅ n-C₇H₁₅ 3891, F H n-C₇H₁₅ CH₃ 3892, F H n-C₇H₁₅ C₂H₅ 3893, F H n-C₇H₁₅ n-C₃H₇ 3894, F H n-C₇H₁₅ n-C₄H₉ 3895, F H n-C₇H₁₅ n-C₅H₁₁ 3896, F H n-C₇H₁₅ n-C₆H₁₃ 3897, F H n-C₇H₁₅ n-C₇H₁₅ 3898, F F n-C₇H₁₅ n-C₇H₁₅ 3899, CF₃ H n-C₇H₁₅ CH₃ 3900, CF₃ H n-C₇H₁₅ C₂H₅ 3901, CF₃ H n-C₇H₁₅ n-C₃H₇ 3902, CF₃ H n-C₇H₁₅ n-C₄H₉ 3903, CF₃ H n-C₇H₁₅ n-C₅H₁₁ 3904, CF₃ H n-C₇H₁₅ n-C₆H₁₃ 3905, CF₃ H n-C₇H₁₅ n-C₇H₁₅ 3906, —OCF₃ H n-C₇H₁₅ CH₃ 3907, —OCF₃ H n-C₇H₁₅ C₂H₅ 3908, —OCF₃ H n-C₇H₁₅ n-C₃H₇ 3909, —OCF₃ H n-C₇H₁₅ n-C₄H₉ 3910, —OCF₃ H n-C₇H₁₅ n-C₅H₁₁ 3911, —OCF₃ H n-C₇H₁₅ n-C₆H₁₃ 3912, —OCF₃ H n-C₇H₁₅ n-C₇H₁₅

TABLE 1 Δε and Δn values for substances of individual examples Example No. Δε Δn 73 -10.2 0.006 106 -10.3 0.068 137 -10.0 0.069 1401 -6.8 0.074 1402 -7.4 0.072 2325 -8.7 0.078 3726 -4.4 0.087 3758 -5.0 0.088 3759 -4.5 0.088 3790 -4.4 0.088 

1. Compound of the general formula I:

in which:

 , independently of one another, stand for

A¹ and A² each, independently of one another, denote 1,4-phenylene, in which ═CH— may be replaced once or twice by ═N— and which may be unsubstituted or mono- to tetrasubstituted, independently of one another, by —CN, F, Cl, Br and/or I, C₁-C₆-alkanyl which is unsubstituted or mono- or polysubstituted by fluorine and/or chlorine or by C₁-C₆-alkoxy which is unsubstituted or mono- or polysubstituted by fluorine and/or chlorine, 1,4-cyclohexylene, 1,4-cyclohexenylene or 1,4-cyclohexadienylene, in which —CH₂— may be replaced once or twice, independently of one another, by —O— or —S— in such a way that hetero atoms are not linked directly and which may be unsubstituted or mono- or polysubstituted by F, Cl, Br and/or I; Z¹ and Z² each, independently of one another, denote a single bond, a double bond, —CF₂O—, —OCF₂—, —CH₂CH₂—, —CF₂CF₂—, —CF₂CH₂—, —CH₂CF₂—, —CHF—CHF—, —C(O)O—, —OC(O)—, —CH₂O—, —OCH₂—, —CF═CH—, —CH═CF—, —CF═CF—, —CH═CH— or —C≡C—; R¹ and R² denote hydrogen, an alkanyl, alkoxy, alkenyl or alkynyl radical having 1 to 15 or 2 to 15 C atoms respectively, each of which is unsubstituted, monosubstituted by —CN or —CF₃ or monosubstituted or polysubstituted by F, Cl, Br and/or I, where, in addition, one or more CH₂ groups in these radicals may each be replaced, independently of one another, by —O—, —S—, —SO₂—, —CO—, —COO—, —OCO— or —OCO—O— in such a way that hetero atoms in the chain are not linked directly, F, Cl, Br, I, —CN, —SCN, —NCS or —SF₅; m and n, independently of one another, are 0, 1, 2 or 3; X¹, X² and Y² each, independently of one another, denote hydrogen, an alkanyl, alkoxy, alkenyl or alkynyl radical having 1 to 15 or 2 to 15 C atoms respectively, each of which is unsubstituted or monosubstituted or polysubstituted by F, Cl, Br and/or I, where, in addition, one or more CH₂ groups in these radicals may each be replaced, independently of one another, by —O—, —S—, —SO₂—, —CO—, —COO—, —OCO— or —OCO—O— in such a way that hetero atoms in the chain are not linked directly, F, Cl, Br, I, —CN, —SF₅, —SCN or —NCS; Y¹ is as defined for Y² or stands for -[-Z³-A³-]_(p)-R³, where Z³ is as defined for Z¹ and Z², A³ is as defined for A¹ and A², R³ is as defined for R¹ and R², and p is as defined for n and m; where A¹, A², A³, Z¹, Z², Z³, R¹, R² and R³ may each have identical or different meanings if m, n and p respectively are greater than 1; Y¹ and Y² may each have identical or different meanings for rings B and B′; and where (a) R¹ does not stand for —COOH if ring B stands for ring f or g and ring B′ stands for ring d and at the same time m is zero and X² is not H, or R² does not stand for —COOH if ring B′ stands for ring f or g and ring B stands for ring d and n is zero and X¹ is not H; (b) R¹-[-A¹-Z¹-]_(m)- and -[-Z²-A²-]-R² are not simultaneously CH₃ if one of X¹ and X² is hydrogen and the other of X¹ and X² is hydrogen or Cl and at the same time both rings B and B′ stand for ring g.
 2. Compound according to claim 1, characterised in that rings B and B′ are each, independently of one another, selected from


3. Compound according to claim 1 characterised in that rings B and B′ are identical, where the radical Y¹ in both rings can have identical or different meanings and the radical Y² in both rings can have identical or different meanings.
 4. Compound according to claim 1, characterised in that the compound of the formula I is selected from the group consisting of compounds of the formulae Iaa, Ibb, Iee, Iff and Igg:

where X¹, X², R¹, R², A¹, A², Z¹, Z², m and n are as defined in claim 1; Y¹¹ and Y¹² are as defined for Y¹ in claim 1 and can have identical or different meanings; and Y²¹ and Y²² are as defined for Y² in claim 1 and can have identical or different meanings.
 5. Compound according to claim 1, characterised in that Y¹ and Y² or Y¹¹, Y¹², Y²¹ and Y²² are simultaneously F.
 6. Compound according to claim 1, characterised in that Z¹ and Z² as well as Z³, independently of one another, are a single bond, —CF₂O—, —OCF₂—, —CF₂CF₂—, —CH═CH—, —CF═CH—, —CH═CF— or —CF═CF—.
 7. Compound according to claim 1, characterised in that A¹ and A² as well as A³, independently of one another, are


8. Compound according to claim 1, characterised in that R¹ and R² as well as R³, independently of one another, are each an alkanyl radical, alkoxy radical or alkenyl radical having 1 to 7 or 2 to 7 C atoms respectively.
 9. Compound according to claim 1, characterised in that m is 0, 1 or 2; n is 0, 1 or 2; m+n is 0, 1, 2 or 3; and p is
 0. 10. Compound according to claim 1, characterised in that at least one of X¹ and X² is F, Cl, CF₃ or OCF₃.
 11. Compound according to claim 1, characterised in that X¹ and X² are F.
 12. Use of a compound according to claim 1 in liquid-crystalline media.
 13. Liquid-crystalline medium comprising at least two liquid-crystalline compounds, characterised in that it comprises at least one compound according to claim
 1. 14. Electro-optical display element containing a liquid-crystalline medium according to claim
 1. 